# Electronic Supplementary Material (ESI) for Dalton Transactions.
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#                                CCDC 
# 
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#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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#  fide research purposes only. It may contain copyright material
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data_Compound-4-h04kcm2

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H18 N2 O2 Si'
_chemical_formula_sum            'C11 H18 N2 O2 Si'
_chemical_formula_weight         238.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   13.0223(2)
_cell_length_b                   17.4770(3)
_cell_length_c                   12.0846(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2750.34(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    42842
_cell_measurement_theta_min      2.910
_cell_measurement_theta_max      27.485

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.151
_exptl_crystal_F_000             1024
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.580
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.161
_shelx_estimated_absorpt_T_min   0.913
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.859
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       '291 1.8 degree images with φ and ω scans'
_diffrn_reflns_number            46491
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_av_R_equivalents  0.0722
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.921
_diffrn_reflns_theta_max         27.477
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             6224
_reflns_number_gt                5000
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.902
_reflns_Friedel_fraction_max     0.983
_reflns_Friedel_fraction_full    0.992

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
;
 DENZO-SCALEPACK Z. Otwinowski and W. Minor, " 
 Processing of X-ray Diffraction Data Collected in Oscillation Mode ", 
 Methods in Enzymology, Volume 276: Macromolecular Crystallography, 
 part A, p.307-326, 1997,C.W. Carter, Jr. & R. M. Sweet, Eds., Academic Press.
;
_computing_structure_solution    
; 
 SIR97- Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C. , 
 Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. 
 (1999) J. Appl. Cryst. 32, 115-119
;
_computing_structure_refinement  
;
 SHELXL-2012 (Sheldrick, 2012)
 Sheldrick GM (2008) Acta Crystallogr A64:112--122 and 
 C. B. Hübschle, G. M. Sheldrick and B. Dittrich
 ShelXle: a Qt graphical user interface for SHELXL
 J. Appl. Cryst., 44, (2011) 1281-1284.
;
_computing_molecular_graphics    
'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565'

_computing_publication_material  
;
 'WinGX publication routines, Farrugia, 
 L. J., J. Appl. Crystallogr., 1999, 32, 837-838
;

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0451P)²+0.2740P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2079 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.01(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6224
_refine_ls_number_parameters     297
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.0897
_refine_ls_wR_factor_gt          0.0819
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.51351(5) 0.92551(4) 0.41217(7) 0.03539(17) Uani 1 1 d . . . . .
N1 N 0.36347(17) 0.66755(12) 0.54761(18) 0.0338(5) Uani 1 1 d . . . . .
N2 N 0.40247(18) 0.79898(12) 0.5253(2) 0.0362(5) Uani 1 1 d . . . . .
O1 O 0.26255(17) 0.75935(12) 0.62486(19) 0.0505(6) Uani 1 1 d . . . . .
O2 O 0.54498(14) 0.83244(9) 0.42872(17) 0.0386(4) Uani 1 1 d . . . . .
C1 C 0.3456(3) 0.5254(2) 0.7442(3) 0.0639(10) Uani 1 1 d . . . . .
H1A H 0.3588 0.4853 0.6931 0.077 Uiso 1 1 calc R U . . .
H1B H 0.3565 0.5175 0.8211 0.077 Uiso 1 1 calc R U . . .
C2 C 0.3127(2) 0.59079(19) 0.7092(3) 0.0465(7) Uani 1 1 d . . . . .
H2 H 0.3000 0.6300 0.7618 0.056 Uiso 1 1 calc R U . . .
C3 C 0.2937(2) 0.60758(16) 0.5891(2) 0.0412(7) Uani 1 1 d . . . . .
H3A H 0.3038 0.5603 0.5453 0.049 Uiso 1 1 calc R U . . .
H3B H 0.2217 0.6244 0.5792 0.049 Uiso 1 1 calc R U . . .
C4 C 0.4515(2) 0.64760(15) 0.4938(2) 0.0339(6) Uani 1 1 d . . . . .
H4 H 0.4672 0.5950 0.4838 0.041 Uiso 1 1 calc R U . . .
C5 C 0.5167(2) 0.70099(14) 0.4545(2) 0.0335(6) Uani 1 1 d . . . . .
C6 C 0.6136(2) 0.68170(18) 0.3928(3) 0.0472(7) Uani 1 1 d . . . . .
H6A H 0.6152 0.7099 0.3228 0.071 Uiso 1 1 calc R U . . .
H6B H 0.6154 0.6266 0.3777 0.071 Uiso 1 1 calc R U . . .
H6C H 0.6732 0.6959 0.4378 0.071 Uiso 1 1 calc R U . . .
C7 C 0.4850(2) 0.77759(15) 0.4725(2) 0.0326(6) Uani 1 1 d . . . . .
C8 C 0.3395(2) 0.74390(15) 0.5691(3) 0.0361(5) Uani 1 1 d . . . . .
C9 C 0.5095(3) 0.97586(17) 0.5460(3) 0.0540(8) Uani 1 1 d . . . . .
H9A H 0.5751 0.9689 0.5845 0.081 Uiso 1 1 calc R U . . .
H9B H 0.4539 0.9549 0.5914 0.081 Uiso 1 1 calc R U . . .
H9C H 0.4975 1.0305 0.5334 0.081 Uiso 1 1 calc R U . . .
C10 C 0.3912(2) 0.9339(2) 0.3367(3) 0.0541(8) Uani 1 1 d . . . . .
H10A H 0.3975 0.9088 0.2645 0.081 Uiso 1 1 calc R U . . .
H10B H 0.3746 0.9881 0.3261 0.081 Uiso 1 1 calc R U . . .
H10C H 0.3365 0.9093 0.3794 0.081 Uiso 1 1 calc R U . . .
C11 C 0.6226(3) 0.95771(19) 0.3260(3) 0.0513(8) Uani 1 1 d . . . . .
H11A H 0.6873 0.9438 0.3621 0.077 Uiso 1 1 calc R U . . .
H11B H 0.6194 1.0134 0.3168 0.077 Uiso 1 1 calc R U . . .
H11C H 0.6188 0.9330 0.2532 0.077 Uiso 1 1 calc R U . . .
Si2 Si 0.70511(6) 0.25790(5) 0.56951(7) 0.0457(2) Uani 1 1 d . . . . .
N3 N 0.41157(17) 0.36876(12) 0.32642(19) 0.0350(5) Uani 1 1 d . . . . .
N4 N 0.54620(17) 0.35098(13) 0.45584(19) 0.0372(5) Uani 1 1 d . . . . .
O3 O 0.45763(16) 0.46382(10) 0.44502(19) 0.0492(5) Uani 1 1 d . . . . .
O4 O 0.62712(15) 0.23591(11) 0.46275(17) 0.0427(5) Uani 1 1 d . . . . .
C21 C 0.3268(3) 0.4683(2) 0.0909(3) 0.0681(11) Uani 1 1 d . . . . .
H21A H 0.2715 0.4351 0.0731 0.082 Uiso 1 1 calc R U . . .
H21B H 0.3536 0.5020 0.0364 0.082 Uiso 1 1 calc R U . . .
C22 C 0.3661(2) 0.46764(18) 0.1907(3) 0.0510(8) Uani 1 1 d . . . . .
H22 H 0.4214 0.5015 0.2062 0.061 Uiso 1 1 calc R U . . .
C23 C 0.3292(2) 0.41714(17) 0.2805(3) 0.0424(7) Uani 1 1 d . . . . .
H23A H 0.2999 0.4490 0.3405 0.051 Uiso 1 1 calc R U . . .
H23B H 0.2738 0.3839 0.2516 0.051 Uiso 1 1 calc R U . . .
C24 C 0.4252(2) 0.29676(15) 0.2866(2) 0.0356(6) Uani 1 1 d . . . . .
H24 H 0.3830 0.2792 0.2277 0.043 Uiso 1 1 calc R U . . .
C25 C 0.4976(2) 0.24952(15) 0.3291(2) 0.0344(6) Uani 1 1 d . . . . .
C26 C 0.5128(3) 0.16849(17) 0.2906(3) 0.0460(7) Uani 1 1 d . . . . .
H26A H 0.5824 0.1626 0.2609 0.069 Uiso 1 1 calc R U . . .
H26B H 0.4626 0.1566 0.2327 0.069 Uiso 1 1 calc R U . . .
H26C H 0.5033 0.1334 0.3531 0.069 Uiso 1 1 calc R U . . .
C27 C 0.55609(18) 0.28132(15) 0.4167(3) 0.0342(5) Uani 1 1 d . . . . .
C28 C 0.4727(2) 0.39840(14) 0.4114(3) 0.0364(6) Uani 1 1 d . . . . .
C29 C 0.7956(3) 0.3323(2) 0.5262(4) 0.0702(11) Uani 1 1 d . . . . .
H29A H 0.8268 0.3179 0.4554 0.105 Uiso 1 1 calc R U . . .
H29B H 0.8495 0.3379 0.5823 0.105 Uiso 1 1 calc R U . . .
H29C H 0.7591 0.3810 0.5178 0.105 Uiso 1 1 calc R U . . .
C30 C 0.6293(4) 0.2849(3) 0.6934(3) 0.0761(13) Uani 1 1 d . . . . .
H30A H 0.5737 0.2478 0.7043 0.114 Uiso 1 1 calc R U . . .
H30B H 0.6000 0.3360 0.6827 0.114 Uiso 1 1 calc R U . . .
H30C H 0.6740 0.2851 0.7586 0.114 Uiso 1 1 calc R U . . .
C31 C 0.7701(3) 0.1641(2) 0.5900(3) 0.0642(10) Uani 1 1 d . . . . .
H31A H 0.7184 0.1239 0.5995 0.096 Uiso 1 1 calc R U . . .
H31B H 0.8137 0.1665 0.6560 0.096 Uiso 1 1 calc R U . . .
H31C H 0.8126 0.1525 0.5252 0.096 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Si1 O2 1.6893(18) . ?
Si1 C10 1.841(3) . ?
Si1 C9 1.842(3) . ?
Si1 C11 1.849(3) . ?
N1 C4 1.363(4) . ?
N1 C8 1.395(3) . ?
N1 C3 1.474(3) . ?
N2 C7 1.305(4) . ?
N2 C8 1.371(4) . ?
O1 C8 1.237(3) . ?
O2 C7 1.344(3) . ?
C1 C2 1.291(5) . ?
C1 H1A 0.9500 . ?
C1 H1B 0.9500 . ?
C2 C3 1.501(4) . ?
C2 H2 0.9500 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.348(4) . ?
C4 H4 0.9500 . ?
C5 C7 1.418(4) . ?
C5 C6 1.503(4) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
Si2 O4 1.686(2) . ?
Si2 C29 1.832(4) . ?
Si2 C30 1.854(4) . ?
Si2 C31 1.862(3) . ?
N3 C24 1.359(4) . ?
N3 C28 1.399(4) . ?
N3 C23 1.474(3) . ?
N4 C27 1.312(3) . ?
N4 C28 1.375(4) . ?
O3 C28 1.229(3) . ?
O4 C27 1.340(3) . ?
C21 C22 1.310(5) . ?
C21 H21A 0.9500 . ?
C21 H21B 0.9500 . ?
C22 C23 1.479(4) . ?
C22 H22 0.9500 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.355(4) . ?
C24 H24 0.9500 . ?
C25 C27 1.417(4) . ?
C25 C26 1.504(4) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Si1 C10 110.20(13) . . ?
O2 Si1 C9 111.27(13) . . ?
C10 Si1 C9 111.87(17) . . ?
O2 Si1 C11 99.98(13) . . ?
C10 Si1 C11 111.17(16) . . ?
C9 Si1 C11 111.77(17) . . ?
C4 N1 C8 121.4(2) . . ?
C4 N1 C3 119.9(2) . . ?
C8 N1 C3 118.6(2) . . ?
C7 N2 C8 118.7(2) . . ?
C7 O2 Si1 126.31(17) . . ?
C2 C1 H1A 120.0 . . ?
C2 C1 H1B 120.0 . . ?
H1A C1 H1B 120.0 . . ?
C1 C2 C3 123.0(3) . . ?
C1 C2 H2 118.5 . . ?
C3 C2 H2 118.5 . . ?
N1 C3 C2 111.5(2) . . ?
N1 C3 H3A 109.3 . . ?
C2 C3 H3A 109.3 . . ?
N1 C3 H3B 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
C5 C4 N1 121.4(2) . . ?
C5 C4 H4 119.3 . . ?
N1 C4 H4 119.3 . . ?
C4 C5 C7 114.6(2) . . ?
C4 C5 C6 123.2(2) . . ?
C7 C5 C6 122.1(2) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 O2 117.8(2) . . ?
N2 C7 C5 125.8(2) . . ?
O2 C7 C5 116.4(2) . . ?
O1 C8 N2 122.8(2) . . ?
O1 C8 N1 119.4(2) . . ?
N2 C8 N1 117.8(2) . . ?
Si1 C9 H9A 109.5 . . ?
Si1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
Si1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
Si1 C10 H10A 109.5 . . ?
Si1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
Si1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
Si1 C11 H11A 109.5 . . ?
Si1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
Si1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O4 Si2 C29 109.32(17) . . ?
O4 Si2 C30 110.78(17) . . ?
C29 Si2 C30 113.1(2) . . ?
O4 Si2 C31 100.07(14) . . ?
C29 Si2 C31 111.74(19) . . ?
C30 Si2 C31 111.05(18) . . ?
C24 N3 C28 121.9(2) . . ?
C24 N3 C23 119.5(2) . . ?
C28 N3 C23 118.5(2) . . ?
C27 N4 C28 119.1(2) . . ?
C27 O4 Si2 126.77(18) . . ?
C22 C21 H21A 120.0 . . ?
C22 C21 H21B 120.0 . . ?
H21A C21 H21B 120.0 . . ?
C21 C22 C23 123.6(3) . . ?
C21 C22 H22 118.2 . . ?
C23 C22 H22 118.2 . . ?
N3 C23 C22 112.5(2) . . ?
N3 C23 H23A 109.1 . . ?
C22 C23 H23A 109.1 . . ?
N3 C23 H23B 109.1 . . ?
C22 C23 H23B 109.1 . . ?
H23A C23 H23B 107.8 . . ?
C25 C24 N3 121.4(3) . . ?
C25 C24 H24 119.3 . . ?
N3 C24 H24 119.3 . . ?
C24 C25 C27 114.7(2) . . ?
C24 C25 C26 123.2(3) . . ?
C27 C25 C26 122.0(2) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N4 C27 O4 117.9(3) . . ?
N4 C27 C25 125.5(2) . . ?
O4 C27 C25 116.7(2) . . ?
O3 C28 N4 122.9(3) . . ?
O3 C28 N3 119.8(2) . . ?
N4 C28 N3 117.4(2) . . ?
Si2 C29 H29A 109.5 . . ?
Si2 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
Si2 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
Si2 C30 H30A 109.5 . . ?
Si2 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
Si2 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
Si2 C31 H31A 109.5 . . ?
Si2 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
Si2 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C4 H4 O3 0.95 2.34 3.267(3) 164.0 .
C24 H24 O1 0.95 2.29 3.197(4) 158.8 3_544

_refine_diff_density_max         0.142
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.037

_shelxl_version_number           2013-3

_database_code_depnum_ccdc_archive 'CCDC 956088'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Compound-5-k04kcm13

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H24 N2 O2 Si'
_chemical_formula_sum            'C17 H24 N2 O2 Si'
_chemical_formula_weight         316.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0964(4)
_cell_length_b                   8.3765(5)
_cell_length_c                   13.0731(7)
_cell_angle_alpha                98.284(3)
_cell_angle_beta                 92.095(3)
_cell_angle_gamma                99.840(2)
_cell_volume                     862.75(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    16108
_cell_measurement_theta_min      2.910
_cell_measurement_theta_max      27.485

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_F_000             340
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.145
_shelx_estimated_absorpt_T_min   0.944
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       '143 2.0 degree images with ω scans'
_diffrn_reflns_number            9597
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         5.533
_diffrn_reflns_theta_max         27.528
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             3883
_reflns_number_gt                3247
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
;
 DENZO-SCALEPACK Z. Otwinowski and W. Minor, " 
 Processing of X-ray Diffraction Data Collected in Oscillation Mode ", 
 Methods in Enzymology, Volume 276: Macromolecular Crystallography, 
 part A, p.307-326, 1997,C.W. Carter, Jr. & R. M. Sweet, Eds., Academic Press.
;
_computing_structure_solution    
; 
 SIR97- Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C. , 
 Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. 
 (1999) J. Appl. Cryst. 32, 115-119
;
_computing_structure_refinement  
;
 SHELXL-2012 (Sheldrick, 2012)
 Sheldrick GM (2008) Acta Crystallogr A64:112--122 and 
 C. B. Hübschle, G. M. Sheldrick and B. Dittrich
 ShelXle: a Qt graphical user interface for SHELXL
 J. Appl. Cryst., 44, (2011) 1281-1284.
;
_computing_molecular_graphics    
'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565'

_computing_publication_material  
;
 'WinGX publication routines, Farrugia, 
 L. J., J. Appl. Crystallogr., 1999, 32, 837-838
;

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0507P)²+0.4022P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3883
_refine_ls_number_parameters     206
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1288
_refine_ls_wR_factor_gt          0.1191
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Si Si -0.17479(6) 0.24545(6) 0.06680(4) 0.03045(15) Uani 1 1 d . . . . .
O1 O 0.98461(14) 0.28759(14) 0.48220(10) 0.0289(3) Uani 1 1 d . . . . .
O2 O 0.57788(15) 0.56988(14) 0.40160(9) 0.0301(3) Uani 1 1 d . . . . .
N1 N 0.77960(16) 0.42408(16) 0.43811(10) 0.0234(3) Uani 1 1 d . . . . .
H1 H 0.851(3) 0.516(3) 0.4578(17) 0.034(5) Uiso 1 1 d . . . . .
N2 N 0.51139(16) 0.28970(17) 0.37729(10) 0.0248(3) Uani 1 1 d . . . . .
C1 C 0.83892(19) 0.28155(19) 0.44763(12) 0.0232(3) Uani 1 1 d . . . . .
C2 C 0.7204(2) 0.13103(19) 0.41593(13) 0.0259(3) Uani 1 1 d . . . . .
C3 C 0.5632(2) 0.14330(19) 0.38329(12) 0.0263(3) Uani 1 1 d . . . . .
H3 H 0.4841 0.0450 0.3634 0.032 Uiso 1 1 calc R U . . .
C4 C 0.61845(19) 0.43695(19) 0.40499(12) 0.0236(3) Uani 1 1 d . . . . .
C5 C 0.7767(2) -0.0293(2) 0.42047(18) 0.0397(4) Uani 1 1 d . . . . .
H5A H 0.6805 -0.1191 0.4033 0.059 Uiso 1 1 calc R U . . .
H5B H 0.8238 -0.0304 0.4904 0.059 Uiso 1 1 calc R U . . .
H5C H 0.8625 -0.0434 0.3706 0.059 Uiso 1 1 calc R U . . .
C6 C 0.3335(2) 0.2905(2) 0.34814(13) 0.0282(3) Uani 1 1 d . . . . .
H6A H 0.3062 0.3984 0.3765 0.034 Uiso 1 1 calc R U . . .
H6B H 0.2618 0.2061 0.3805 0.034 Uiso 1 1 calc R U . . .
C7 C 0.2911(2) 0.2583(2) 0.23244(13) 0.0286(3) Uani 1 1 d . . . . .
H7A H 0.3146 0.1492 0.2034 0.034 Uiso 1 1 calc R U . . .
H7B H 0.3623 0.3418 0.1991 0.034 Uiso 1 1 calc R U . . .
C8 C 0.1063(2) 0.2643(2) 0.20954(13) 0.0301(4) Uani 1 1 d . . . . .
H8A H 0.0821 0.3698 0.2448 0.036 Uiso 1 1 calc R U . . .
H8B H 0.0366 0.1752 0.2391 0.036 Uiso 1 1 calc R U . . .
C9 C 0.0548(2) 0.2470(2) 0.09417(13) 0.0334(4) Uani 1 1 d . . . . .
H9A H 0.0834 0.1439 0.0583 0.040 Uiso 1 1 calc R U . . .
H9B H 0.1207 0.3389 0.0652 0.040 Uiso 1 1 calc R U . . .
C10 C -0.3010(2) 0.0588(3) 0.10621(16) 0.0407(4) Uani 1 1 d . . . . .
H10A H -0.2726 0.0552 0.1793 0.061 Uiso 1 1 calc R U . . .
H10B H -0.2759 -0.0392 0.0635 0.061 Uiso 1 1 calc R U . . .
H10C H -0.4209 0.0624 0.0966 0.061 Uiso 1 1 calc R U . . .
C11 C -0.2385(3) 0.4307(3) 0.14010(15) 0.0419(4) Uani 1 1 d . . . . .
H11A H -0.3595 0.4257 0.1272 0.063 Uiso 1 1 calc R U . . .
H11B H -0.1770 0.5293 0.1173 0.063 Uiso 1 1 calc R U . . .
H11C H -0.2126 0.4346 0.2143 0.063 Uiso 1 1 calc R U . . .
C12 C -0.2199(2) 0.2474(2) -0.07516(13) 0.0295(3) Uani 1 1 d . . . . .
C13 C -0.1080(2) 0.2116(2) -0.15074(14) 0.0362(4) Uani 1 1 d . . . . .
H13 H -0.0052 0.1808 -0.1310 0.043 Uiso 1 1 calc R U . . .
C14 C -0.1456(3) 0.2205(3) -0.25500(15) 0.0409(4) Uani 1 1 d . . . . .
H14 H -0.0675 0.1968 -0.3050 0.049 Uiso 1 1 calc R U . . .
C15 C -0.2935(2) 0.2629(2) -0.28546(14) 0.0353(4) Uani 1 1 d . . . . .
H15 H -0.3172 0.2703 -0.3562 0.042 Uiso 1 1 calc R U . . .
C16 C -0.4089(2) 0.2952(2) -0.21257(14) 0.0355(4) Uani 1 1 d . . . . .
H16 H -0.5138 0.3205 -0.2336 0.043 Uiso 1 1 calc R U . . .
C17 C -0.3702(2) 0.2904(2) -0.10844(14) 0.0341(4) Uani 1 1 d . . . . .
H17 H -0.4479 0.3169 -0.0588 0.041 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Si C11 1.864(2) . ?
Si C10 1.865(2) . ?
Si C9 1.8772(18) . ?
Si C12 1.8812(18) . ?
O1 C1 1.2378(19) . ?
O2 C4 1.2198(19) . ?
N1 C1 1.381(2) . ?
N1 C4 1.3862(19) . ?
N1 H1 0.88(2) . ?
N2 C4 1.374(2) . ?
N2 C3 1.374(2) . ?
N2 C6 1.4778(19) . ?
C1 C2 1.445(2) . ?
C2 C3 1.353(2) . ?
C2 C5 1.499(2) . ?
C3 H3 0.9500 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.514(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.526(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.530(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C17 1.398(2) . ?
C12 C13 1.400(2) . ?
C13 C14 1.401(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.368(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.390(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.394(2) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 Si C10 108.89(10) . . ?
C11 Si C9 110.55(9) . . ?
C10 Si C9 109.67(9) . . ?
C11 Si C12 107.86(9) . . ?
C10 Si C12 109.74(8) . . ?
C9 Si C12 110.11(8) . . ?
C1 N1 C4 126.83(14) . . ?
C1 N1 H1 116.3(14) . . ?
C4 N1 H1 116.8(14) . . ?
C4 N2 C3 121.48(13) . . ?
C4 N2 C6 118.77(13) . . ?
C3 N2 C6 119.59(13) . . ?
O1 C1 N1 120.31(14) . . ?
O1 C1 C2 124.05(14) . . ?
N1 C1 C2 115.64(13) . . ?
C3 C2 C1 117.59(14) . . ?
C3 C2 C5 123.44(15) . . ?
C1 C2 C5 118.97(14) . . ?
C2 C3 N2 123.80(15) . . ?
C2 C3 H3 118.1 . . ?
N2 C3 H3 118.1 . . ?
O2 C4 N2 123.82(14) . . ?
O2 C4 N1 121.56(14) . . ?
N2 C4 N1 114.63(13) . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 C7 113.86(13) . . ?
N2 C6 H6A 108.8 . . ?
C7 C6 H6A 108.8 . . ?
N2 C6 H6B 108.8 . . ?
C7 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
C6 C7 C8 110.25(13) . . ?
C6 C7 H7A 109.6 . . ?
C8 C7 H7A 109.6 . . ?
C6 C7 H7B 109.6 . . ?
C8 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
C7 C8 C9 114.09(14) . . ?
C7 C8 H8A 108.7 . . ?
C9 C8 H8A 108.7 . . ?
C7 C8 H8B 108.7 . . ?
C9 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C8 C9 Si 113.66(12) . . ?
C8 C9 H9A 108.8 . . ?
Si C9 H9A 108.8 . . ?
C8 C9 H9B 108.8 . . ?
Si C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
Si C10 H10A 109.5 . . ?
Si C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
Si C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
Si C11 H11A 109.5 . . ?
Si C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
Si C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C12 C13 117.22(16) . . ?
C17 C12 Si 119.44(13) . . ?
C13 C12 Si 123.32(13) . . ?
C12 C13 C14 120.93(17) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C15 C14 C13 120.65(18) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 119.74(17) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C17 119.71(17) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C12 121.70(17) . . ?
C16 C17 H17 119.2 . . ?
C12 C17 H17 119.2 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.88(2) 1.97(2) 2.8490(18) 173(2) 2_766


_refine_diff_density_max         0.305
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.047

_shelxl_version_number           2013-3

_database_code_depnum_ccdc_archive 'CCDC 956089'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Compound-8-bath158

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H23 N3 O Si'
_chemical_formula_sum            'C16 H23 N3 O Si'
_chemical_formula_weight         301.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.5090(15)
_cell_length_b                   40.651(6)
_cell_length_c                   8.7418(13)
_cell_angle_alpha                90
_cell_angle_beta                 98.108(3)
_cell_angle_gamma                90
_cell_volume                     3345.3(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1885
_cell_measurement_theta_min      3.578
_cell_measurement_theta_max      26.73

_exptl_crystal_description       colorless
_exptl_crystal_colour            plate
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_F_000             1296

_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.221
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.846
_diffrn_radiation_type           'Synchrotron - Daresbury SRS station 16.2 SMX'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_measurement_device_type  'Bruker APEXII diffractometer'
_diffrn_measurement_method       'ω rotation with narrow frames'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21914
_diffrn_reflns_av_unetI/netI     0.0711
_diffrn_reflns_av_R_equivalents  0.0641
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -48
_diffrn_reflns_limit_k_max       46
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.238
_diffrn_reflns_theta_max         30.236
_diffrn_reflns_theta_full        30.504
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.964
_reflns_number_total             5856
_reflns_number_gt                3824
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'local programs'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'

_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    
'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565'

_computing_publication_material  'SHELXL-97/2 (Sheldrick,1997)'


_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0770P)²+0.6550P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5856
_refine_ls_number_parameters     395
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0585
_refine_ls_wR_factor_ref         0.1759
_refine_ls_wR_factor_gt          0.1540
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.81825(8) 0.15167(2) 0.21557(9) 0.0281(2) Uani 1 1 d . . . . .
Si2 Si 0.67795(9) -0.15334(2) -1.69746(9) 0.0317(2) Uani 1 1 d . . . . .
O1 O 0.70017(19) 0.03427(5) -0.3795(2) 0.0341(5) Uani 1 1 d . . . . .
O2 O 0.79994(19) -0.03341(5) -1.1176(2) 0.0370(5) Uani 1 1 d . . . . .
N1 N 0.9314(2) 0.04975(5) -0.3583(2) 0.0203(5) Uani 1 1 d . . . . .
N2 N 0.8100(2) 0.02750(5) -0.5922(2) 0.0209(5) Uani 1 1 d . . . . .
N3 N 0.9264(2) 0.02039(5) -0.8016(3) 0.0239(5) Uani 1 1 d D . . . .
H3A H 0.856(2) 0.0066(6) -0.834(3) 0.029 Uiso 1 1 d D U . . .
H3B H 1.000(2) 0.0229(7) -0.843(3) 0.029 Uiso 1 1 d D U . . .
N4 N 0.5673(2) -0.04788(5) -1.1377(2) 0.0210(5) Uani 1 1 d . . . . .
N5 N 0.6929(2) -0.02734(5) -0.9026(2) 0.0220(5) Uani 1 1 d . . . . .
N6 N 0.5786(2) -0.02088(5) -0.6905(2) 0.0235(5) Uani 1 1 d D . . . .
H6A H 0.650(2) -0.0078(6) -0.658(3) 0.028 Uiso 1 1 d D U . . .
H6B H 0.501(2) -0.0232(6) -0.651(3) 0.028 Uiso 1 1 d D U . . .
C1 C 0.9286(3) 0.03078(6) -0.6558(3) 0.0191(5) Uani 1 1 d . . . . .
C2 C 1.0545(3) 0.04468(6) -0.5738(3) 0.0234(6) Uani 1 1 d . . . . .
H2 H 1.1373 0.0478 -0.6216 0.028 Uiso 1 1 calc R U . . .
C3 C 1.0511(3) 0.05324(6) -0.4252(3) 0.0242(6) Uani 1 1 d . . . . .
H3 H 1.1343 0.0619 -0.3660 0.029 Uiso 1 1 calc R U . . .
C4 C 0.8087(3) 0.03685(6) -0.4428(3) 0.0222(6) Uani 1 1 d . . . . .
C5 C 0.9310(3) 0.05874(6) -0.1947(3) 0.0247(6) Uani 1 1 d . . . . .
H5A H 1.0300 0.0592 -0.1415 0.030 Uiso 1 1 calc R U . . .
H5B H 0.8789 0.0417 -0.1444 0.030 Uiso 1 1 calc R U . . .
C6 C 0.8624(3) 0.09213(6) -0.1761(3) 0.0256(6) Uani 1 1 d . . . . .
H6C H 0.7606 0.0911 -0.2198 0.031 Uiso 1 1 calc R U . . .
H6D H 0.9082 0.1088 -0.2350 0.031 Uiso 1 1 calc R U . . .
C7 C 0.8758(3) 0.10264(6) -0.0066(3) 0.0260(6) Uani 1 1 d . . . . .
H7A H 0.8510 0.0838 0.0560 0.031 Uiso 1 1 calc R U . . .
H7B H 0.9758 0.1086 0.0299 0.031 Uiso 1 1 calc R U . . .
C8 C 0.7805(3) 0.13179(7) 0.0197(3) 0.0300(6) Uani 1 1 d . . . . .
H8A H 0.6805 0.1242 0.0040 0.036 Uiso 1 1 calc R U . . .
H8B H 0.7901 0.1487 -0.0598 0.036 Uiso 1 1 calc R U . . .
C9 C 0.9962(3) 0.17147(7) 0.2303(4) 0.0435(8) Uani 1 1 d . . . . .
H9A H 1.0177 0.1826 0.3304 0.065 Uiso 1 1 calc R U . . .
H9B H 0.9962 0.1876 0.1471 0.065 Uiso 1 1 calc R U . . .
H9C H 1.0685 0.1547 0.2212 0.065 Uiso 1 1 calc R U . . .
C10 C 0.8155(4) 0.12067(7) 0.3726(3) 0.0455(8) Uani 1 1 d . . . . .
H10A H 0.8345 0.1316 0.4733 0.068 Uiso 1 1 calc R U . . .
H10B H 0.8887 0.1040 0.3650 0.068 Uiso 1 1 calc R U . . .
H10C H 0.7220 0.1101 0.3621 0.068 Uiso 1 1 calc R U . . .
C11 C 0.6792(3) 0.18344(7) 0.2406(3) 0.0333(7) Uani 1 1 d . . . . .
C12 C 0.7091(4) 0.20941(8) 0.3438(4) 0.0516(9) Uani 1 1 d . . . . .
H12 H 0.8027 0.2116 0.3975 0.062 Uiso 1 1 calc R U . . .
C13 C 0.6063(4) 0.23227(8) 0.3708(5) 0.0627(11) Uani 1 1 d . . . . .
H13 H 0.6307 0.2497 0.4422 0.075 Uiso 1 1 calc R U . . .
C14 C 0.4708(4) 0.22984(9) 0.2954(5) 0.0595(10) Uani 1 1 d . . . . .
H14 H 0.4008 0.2455 0.3134 0.071 Uiso 1 1 calc R U . . .
C15 C 0.4372(4) 0.20430(9) 0.1926(5) 0.0632(11) Uani 1 1 d . . . . .
H15 H 0.3434 0.2023 0.1391 0.076 Uiso 1 1 calc R U . . .
C16 C 0.5403(3) 0.18150(8) 0.1675(4) 0.0523(9) Uani 1 1 d . . . . .
H16 H 0.5147 0.1639 0.0976 0.063 Uiso 1 1 calc R U . . .
C17 C 0.5745(3) -0.03057(6) -0.8368(3) 0.0181(5) Uani 1 1 d . . . . .
C18 C 0.4475(3) -0.04401(6) -0.9201(3) 0.0238(6) Uani 1 1 d . . . . .
H18 H 0.3653 -0.0474 -0.8717 0.029 Uiso 1 1 calc R U . . .
C19 C 0.4485(3) -0.05169(6) -1.0694(3) 0.0235(6) Uani 1 1 d . . . . .
H19 H 0.3644 -0.0599 -1.1284 0.028 Uiso 1 1 calc R U . . .
C20 C 0.6922(3) -0.03585(6) -1.0535(3) 0.0228(6) Uani 1 1 d . . . . .
C21 C 0.5654(3) -0.05705(6) -1.3011(3) 0.0255(6) Uani 1 1 d . . . . .
H21A H 0.6206 -0.0407 -1.3519 0.031 Uiso 1 1 calc R U . . .
H21B H 0.4663 -0.0566 -1.3541 0.031 Uiso 1 1 calc R U . . .
C22 C 0.6279(3) -0.09108(6) -1.3172(3) 0.0271(6) Uani 1 1 d . . . . .
H22A H 0.5775 -0.1071 -1.2590 0.033 Uiso 1 1 calc R U . . .
H22B H 0.7291 -0.0909 -1.2709 0.033 Uiso 1 1 calc R U . . .
C23 C 0.6169(3) -0.10229(7) -1.4855(3) 0.0288(6) Uani 1 1 d . . . . .
H23A H 0.5164 -0.1072 -1.5250 0.035 Uiso 1 1 calc R U . . .
H23B H 0.6479 -0.0841 -1.5485 0.035 Uiso 1 1 calc R U . . .
C24 C 0.7071(3) -0.13270(7) -1.5044(3) 0.0346(7) Uani 1 1 d . . . . .
H24A H 0.6891 -0.1490 -1.4253 0.041 Uiso 1 1 calc R U . . .
H24B H 0.8084 -0.1263 -1.4822 0.041 Uiso 1 1 calc R U . . .
C25 C 0.4990(3) -0.17270(8) -1.7217(4) 0.0484(8) Uani 1 1 d . . . . .
H25A H 0.4830 -0.1845 -1.8204 0.073 Uiso 1 1 calc R U . . .
H25B H 0.4264 -0.1556 -1.7205 0.073 Uiso 1 1 calc R U . . .
H25C H 0.4933 -0.1882 -1.6369 0.073 Uiso 1 1 calc R U . . .
C26 C 0.6967(3) -0.12326(7) -1.8551(3) 0.0424(8) Uani 1 1 d . . . . .
H26A H 0.6906 -0.1349 -1.9539 0.064 Uiso 1 1 calc R U . . .
H26B H 0.7888 -0.1122 -1.8333 0.064 Uiso 1 1 calc R U . . .
H26C H 0.6204 -0.1069 -1.8607 0.064 Uiso 1 1 calc R U . . .
C27 C 0.8181(3) -0.18602(7) -1.6955(3) 0.0367(7) Uani 1 1 d . . . . .
C28 C 0.8098(4) -0.21479(7) -1.6085(4) 0.0472(8) Uani 1 1 d . . . . .
H28 H 0.7299 -0.2179 -1.5560 0.057 Uiso 1 1 calc R U . . .
C29 C 0.9146(4) -0.23881(8) -1.5968(4) 0.0553(10) Uani 1 1 d . . . . .
H29 H 0.9061 -0.2581 -1.5373 0.066 Uiso 1 1 calc R U . . .
C30 C 1.0321(4) -0.23440(9) -1.6728(5) 0.0581(10) Uani 1 1 d . . . . .
H30 H 1.1035 -0.2509 -1.6667 0.070 Uiso 1 1 calc R U . . .
C31 C 1.0450(4) -0.20645(9) -1.7560(5) 0.0614(10) Uani 1 1 d . . . . .
H31 H 1.1266 -0.2032 -1.8057 0.074 Uiso 1 1 calc R U . . .
C32 C 0.9383(4) -0.18259(8) -1.7683(4) 0.0514(9) Uani 1 1 d . . . . .
H32 H 0.9481 -0.1634 -1.8281 0.062 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Si1 C9 1.862(3) . ?
Si1 C10 1.867(3) . ?
Si1 C8 1.881(3) . ?
Si1 C11 1.883(3) . ?
Si2 C25 1.859(3) . ?
Si2 C26 1.869(3) . ?
Si2 C24 1.870(3) . ?
Si2 C27 1.880(3) . ?
O1 C4 1.242(3) . ?
O2 C20 1.239(3) . ?
N1 C3 1.358(3) . ?
N1 C4 1.393(3) . ?
N1 C5 1.477(3) . ?
N2 C1 1.333(3) . ?
N2 C4 1.362(3) . ?
N3 C1 1.340(3) . ?
N3 H3A 0.885(17) . ?
N3 H3B 0.839(17) . ?
N4 C19 1.359(3) . ?
N4 C20 1.395(3) . ?
N4 C21 1.474(3) . ?
N5 C17 1.341(3) . ?
N5 C20 1.363(3) . ?
N6 C17 1.334(3) . ?
N6 H6A 0.877(17) . ?
N6 H6B 0.858(17) . ?
C1 C2 1.423(3) . ?
C2 C3 1.350(3) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C5 C6 1.525(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.530(3) . ?
C6 H6C 0.9900 . ?
C6 H6D 0.9900 . ?
C7 C8 1.528(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C16 1.386(4) . ?
C11 C12 1.391(4) . ?
C12 C13 1.393(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.366(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.381(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.389(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.428(3) . ?
C18 C19 1.343(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C21 C22 1.520(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.529(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.527(4) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C32 1.391(4) . ?
C27 C28 1.403(4) . ?
C28 C29 1.389(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.390(5) . ?
C29 H29 0.9500 . ?
C30 C31 1.365(5) . ?
C30 H30 0.9500 . ?
C31 C32 1.397(5) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 Si1 C10 110.35(15) . . ?
C9 Si1 C8 107.68(14) . . ?
C10 Si1 C8 111.02(13) . . ?
C9 Si1 C11 109.97(13) . . ?
C10 Si1 C11 107.14(13) . . ?
C8 Si1 C11 110.69(12) . . ?
C25 Si2 C26 111.94(15) . . ?
C25 Si2 C24 108.03(15) . . ?
C26 Si2 C24 110.75(14) . . ?
C25 Si2 C27 109.76(14) . . ?
C26 Si2 C27 109.13(14) . . ?
C24 Si2 C27 107.10(12) . . ?
C3 N1 C4 120.1(2) . . ?
C3 N1 C5 120.5(2) . . ?
C4 N1 C5 119.3(2) . . ?
C1 N2 C4 119.7(2) . . ?
C1 N3 H3A 114.2(18) . . ?
C1 N3 H3B 118.1(19) . . ?
H3A N3 H3B 125(3) . . ?
C19 N4 C20 120.4(2) . . ?
C19 N4 C21 120.0(2) . . ?
C20 N4 C21 119.6(2) . . ?
C17 N5 C20 120.0(2) . . ?
C17 N6 H6A 113.9(18) . . ?
C17 N6 H6B 116.0(19) . . ?
H6A N6 H6B 127(3) . . ?
N2 C1 N3 117.7(2) . . ?
N2 C1 C2 122.1(2) . . ?
N3 C1 C2 120.2(2) . . ?
C3 C2 C1 117.0(2) . . ?
C3 C2 H2 121.5 . . ?
C1 C2 H2 121.5 . . ?
C2 C3 N1 121.5(2) . . ?
C2 C3 H3 119.2 . . ?
N1 C3 H3 119.2 . . ?
O1 C4 N2 121.6(2) . . ?
O1 C4 N1 118.8(2) . . ?
N2 C4 N1 119.5(2) . . ?
N1 C5 C6 112.5(2) . . ?
N1 C5 H5A 109.1 . . ?
C6 C5 H5A 109.1 . . ?
N1 C5 H5B 109.1 . . ?
C6 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
C5 C6 C7 111.9(2) . . ?
C5 C6 H6C 109.2 . . ?
C7 C6 H6C 109.2 . . ?
C5 C6 H6D 109.2 . . ?
C7 C6 H6D 109.2 . . ?
H6C C6 H6D 107.9 . . ?
C8 C7 C6 113.1(2) . . ?
C8 C7 H7A 109.0 . . ?
C6 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C7 C8 Si1 115.39(17) . . ?
C7 C8 H8A 108.4 . . ?
Si1 C8 H8A 108.4 . . ?
C7 C8 H8B 108.4 . . ?
Si1 C8 H8B 108.4 . . ?
H8A C8 H8B 107.5 . . ?
Si1 C9 H9A 109.5 . . ?
Si1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
Si1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
Si1 C10 H10A 109.5 . . ?
Si1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
Si1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 C11 C12 115.9(3) . . ?
C16 C11 Si1 123.1(2) . . ?
C12 C11 Si1 120.9(2) . . ?
C11 C12 C13 122.1(3) . . ?
C11 C12 H12 118.9 . . ?
C13 C12 H12 118.9 . . ?
C14 C13 C12 120.4(3) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 119.0(3) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C14 C15 C16 120.0(3) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C11 C16 C15 122.5(3) . . ?
C11 C16 H16 118.8 . . ?
C15 C16 H16 118.8 . . ?
N6 C17 N5 118.0(2) . . ?
N6 C17 C18 120.7(2) . . ?
N5 C17 C18 121.3(2) . . ?
C19 C18 C17 117.6(2) . . ?
C19 C18 H18 121.2 . . ?
C17 C18 H18 121.2 . . ?
C18 C19 N4 121.4(2) . . ?
C18 C19 H19 119.3 . . ?
N4 C19 H19 119.3 . . ?
O2 C20 N5 121.8(2) . . ?
O2 C20 N4 119.1(2) . . ?
N5 C20 N4 119.2(2) . . ?
N4 C21 C22 111.6(2) . . ?
N4 C21 H21A 109.3 . . ?
C22 C21 H21A 109.3 . . ?
N4 C21 H21B 109.3 . . ?
C22 C21 H21B 109.3 . . ?
H21A C21 H21B 108.0 . . ?
C21 C22 C23 112.7(2) . . ?
C21 C22 H22A 109.1 . . ?
C23 C22 H22A 109.1 . . ?
C21 C22 H22B 109.1 . . ?
C23 C22 H22B 109.1 . . ?
H22A C22 H22B 107.8 . . ?
C24 C23 C22 112.5(2) . . ?
C24 C23 H23A 109.1 . . ?
C22 C23 H23A 109.1 . . ?
C24 C23 H23B 109.1 . . ?
C22 C23 H23B 109.1 . . ?
H23A C23 H23B 107.8 . . ?
C23 C24 Si2 116.54(18) . . ?
C23 C24 H24A 108.2 . . ?
Si2 C24 H24A 108.2 . . ?
C23 C24 H24B 108.2 . . ?
Si2 C24 H24B 108.2 . . ?
H24A C24 H24B 107.3 . . ?
Si2 C25 H25A 109.5 . . ?
Si2 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
Si2 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
Si2 C26 H26A 109.5 . . ?
Si2 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
Si2 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C32 C27 C28 116.4(3) . . ?
C32 C27 Si2 123.5(2) . . ?
C28 C27 Si2 120.0(2) . . ?
C29 C28 C27 122.1(3) . . ?
C29 C28 H28 119.0 . . ?
C27 C28 H28 119.0 . . ?
C28 C29 C30 119.4(3) . . ?
C28 C29 H29 120.3 . . ?
C30 C29 H29 120.3 . . ?
C31 C30 C29 120.1(3) . . ?
C31 C30 H30 120.0 . . ?
C29 C30 H30 120.0 . . ?
C30 C31 C32 120.0(4) . . ?
C30 C31 H31 120.0 . . ?
C32 C31 H31 120.0 . . ?
C27 C32 C31 122.0(3) . . ?
C27 C32 H32 119.0 . . ?
C31 C32 H32 119.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3A N5 0.885(17) 2.102(17) 2.987(3) 178(2) .
N3 H3B O2 0.839(17) 2.026(18) 2.840(3) 164(3) 3_753
N6 H6A N2 0.877(17) 2.112(17) 2.986(3) 174(2) .
N6 H6B O1 0.858(17) 2.022(18) 2.855(3) 163(3) 3_654
C2 H2 O2 0.95 2.51 3.233(3) 133.4 3_753
C18 H18 O1 0.95 2.42 3.166(3) 134.8 3_654

_refine_diff_density_max         0.419
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.058

_shelxl_version_number           2013-3

_database_code_depnum_ccdc_archive 'CCDC 956090'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Compound-9-h06kcm14

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H28 N5 Ni0.50 O2 S2 Si'
_chemical_formula_weight         480.03

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3500(4)
_cell_length_b                   11.0160(6)
_cell_length_c                   14.6670(8)
_cell_angle_alpha                103.051(3)
_cell_angle_beta                 94.631(3)
_cell_angle_gamma                107.523(2)
_cell_volume                     1237.12(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    32908
_cell_measurement_theta_min      2.910
_cell_measurement_theta_max      27.485

_exptl_crystal_description       plate
_exptl_crystal_colour            pink
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             506
_exptl_absorpt_coefficient_mu    0.656
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12877
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_av_unetI/netI     0.0651
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         5.85
_diffrn_reflns_theta_max         27.48
_reflns_number_total             5522
_reflns_number_gt                3754
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        'Denzo & Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEX (P.McArdle, 1995)'
_computing_publication_material  'SHELXL-97/2 (Sheldrick,1997)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

The asymmetric unit consists of half a nickel complex (in which the 
metal centre is located at a crystallographic inversion centre) and 
one heavily disordered silylated thymine unit.  The flexible arm of 
the thymine functionality (C9-18 and the silicon) exhibited extensive 
disorder which is modelled over 3 sites in a 40:30:30 ratio. Only the
phenyl component attached to the 40% occupancy silicon (Si1) could be 
located with any reliability, and this is included subject to the 
restraint of being treated as a rigid hexagon. In the cases of 
Si1A and Si1B, only the ipso carbon of the phenyl component is 
included in the refinement, as the disorder proximate to these 
centres has resulted in substantial smearing of the electron 
density. Anisotropic refinement was confined to the fractional 
occupancy silicons and C12-13 in this disordered region.
 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1204P)²+1.8675P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5522
_refine_ls_number_parameters     266
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.1135
_refine_ls_R_factor_gt           0.0772
_refine_ls_wR_factor_ref         0.2361
_refine_ls_wR_factor_gt          0.2032
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.5000 0.5000 0.5000 0.0419(3) Uani 1 2 d S . .
S1 S 0.45196(13) 0.62922(11) 0.41952(10) 0.0533(4) Uani 1 1 d . . .
S2 S 0.74450(13) 0.50928(10) 0.45674(10) 0.0507(3) Uani 1 1 d . . .
Si1 Si 0.5891(14) 0.9651(10) 0.0297(7) 0.153(3) Uani 0.40 1 d PD A -1
Si1A Si 0.9545(14) 1.5772(7) 0.1271(5) 0.107(3) Uani 0.30 1 d PD A -2
Si1B Si 0.7104(14) 1.5119(10) 0.1164(5) 0.116(3) Uani 0.30 1 d PD B -3
O1 O 0.8426(4) 1.0685(4) 0.3534(4) 0.0809(14) Uani 1 1 d . . .
O2 O 1.2699(4) 0.9020(3) 0.3937(3) 0.0520(8) Uani 1 1 d . . .
N1 N 0.6038(5) 0.8520(4) 0.3898(3) 0.0547(10) Uani 1 1 d . . .
H1A H 0.6879 0.9183 0.3826 0.066 Uiso 1 1 calc R . .
H1B H 0.4989 0.8538 0.3830 0.066 Uiso 1 1 calc R . .
N2 N 0.7986(4) 0.7550(3) 0.4198(3) 0.0426(8) Uani 1 1 d . . .
N3 N 1.0183(5) 0.6782(4) 0.4354(3) 0.0536(10) Uani 1 1 d . . .
H3A H 1.0844 0.7510 0.4250 0.064 Uiso 1 1 calc R . .
H3B H 1.0614 0.6178 0.4457 0.064 Uiso 1 1 calc R . .
N4 N 1.0608(4) 0.9891(4) 0.3740(3) 0.0489(9) Uani 1 1 d . . .
H4 H 0.9903 0.9200 0.3868 0.059 Uiso 1 1 calc R . .
N5 N 1.1061(4) 1.1874(4) 0.3331(3) 0.0492(9) Uani 1 1 d . . .
C1 C 0.6352(5) 0.7496(4) 0.4108(3) 0.0431(9) Uani 1 1 d . . .
C2 C 0.8532(5) 0.6593(4) 0.4358(3) 0.0430(9) Uani 1 1 d . . .
C3 C 0.9936(6) 1.0812(5) 0.3541(4) 0.0572(13) Uani 1 1 d . . .
C4 C 1.2282(5) 0.9943(4) 0.3758(4) 0.0468(10) Uani 1 1 d . . .
C5 C 1.3398(5) 1.1087(4) 0.3543(4) 0.0490(11) Uani 1 1 d . . .
C6 C 1.5243(6) 1.1228(5) 0.3572(5) 0.0611(14) Uani 1 1 d . . .
H6A H 1.5861 1.2083 0.3468 0.092 Uiso 1 1 calc R . .
H6B H 1.5367 1.0518 0.3074 0.092 Uiso 1 1 calc R . .
H6C H 1.5708 1.1178 0.4192 0.092 Uiso 1 1 calc R . .
C7 C 1.2736(5) 1.1986(4) 0.3349(4) 0.0477(10) Uani 1 1 d . . .
H7 H 1.3477 1.2745 0.3215 0.057 Uiso 1 1 calc R . .
C8 C 1.0418(6) 1.2884(5) 0.3089(4) 0.0601(13) Uani 1 1 d D . .
H8A H 1.1248 1.3779 0.3367 0.072 Uiso 1 1 calc R A .
H8B H 0.9325 1.2844 0.3318 0.072 Uiso 1 1 calc R . .
C9 C 1.017(4) 1.253(3) 0.1985(7) 0.119(8) Uiso 0.40 1 d PD A -1
H9A H 0.9668 1.3177 0.1827 0.142 Uiso 0.40 1 calc PR A -1
H9B H 1.1353 1.2814 0.1849 0.142 Uiso 0.40 1 calc PR A -1
C10 C 0.932(5) 1.132(4) 0.122(3) 0.175(13) Uiso 0.40 1 d P A -1
H10A H 0.9837 1.1384 0.0640 0.210 Uiso 0.40 1 calc PR A -1
H10B H 0.9444 1.0548 0.1409 0.210 Uiso 0.40 1 calc PR A -1
C11 C 0.754(4) 1.118(3) 0.103(3) 0.181(14) Uiso 0.40 1 d PD A -1
H11A H 0.7481 1.1892 0.0731 0.217 Uiso 0.40 1 calc PR A -1
H11B H 0.7171 1.1381 0.1651 0.217 Uiso 0.40 1 calc PR A -1
C12 C 0.655(8) 0.856(5) 0.093(4) 0.26(2) Uani 0.40 1 d PDU A -1
H12A H 0.7432 0.8277 0.0626 0.392 Uiso 0.40 1 calc PR A -1
H12B H 0.5566 0.7785 0.0894 0.392 Uiso 0.40 1 calc PR A -1
H12C H 0.7004 0.9041 0.1591 0.392 Uiso 0.40 1 calc PR A -1
C13 C 0.612(4) 0.929(3) -0.0971(15) 0.149(11) Uani 0.40 1 d PD A -1
H13A H 0.5723 0.9880 -0.1270 0.223 Uiso 0.40 1 calc PR A -1
H13B H 0.5446 0.8372 -0.1288 0.223 Uiso 0.40 1 calc PR A -1
H13C H 0.7323 0.9429 -0.1027 0.223 Uiso 0.40 1 calc PR A -1
C14 C 0.3727(15) 0.9688(13) 0.0466(11) 0.127(8) Uiso 0.40 1 d PGD A -1
C15 C 0.2705(16) 0.9003(15) 0.1011(14) 0.195(16) Uiso 0.40 1 d PG A -1
H15 H 0.3097 0.8455 0.1324 0.233 Uiso 0.40 1 calc PR A -1
C16 C 0.1110(15) 0.912(2) 0.1098(16) 0.24(2) Uiso 0.40 1 d PG A -1
H16 H 0.0411 0.8653 0.1471 0.291 Uiso 0.40 1 calc PR A -1
C17 C 0.0536(12) 0.992(2) 0.0640(16) 0.23(2) Uiso 0.40 1 d PG A -1
H17 H -0.0555 1.0003 0.0700 0.278 Uiso 0.40 1 calc PR A -1
C18 C 0.1558(12) 1.0607(19) 0.0095(14) 0.24(2) Uiso 0.40 1 d PG A -1
H18 H 0.1166 1.1155 -0.0218 0.289 Uiso 0.40 1 calc PR A -1
C19 C 0.3154(13) 1.0490(15) 0.0007(11) 0.145(12) Uiso 0.40 1 d PG A -1
H19 H 0.3852 1.0957 -0.0365 0.174 Uiso 0.40 1 calc PR A -1
C9A C 0.9485(13) 1.2457(13) 0.2082(6) 0.041(3) Uiso 0.30 1 d PGD A -2
H9A1 H 1.0216 1.2112 0.1669 0.049 Uiso 0.30 1 calc PR A -2
H9A2 H 0.8450 1.1703 0.2044 0.049 Uiso 0.30 1 calc PR A -2
C10A C 0.8983(12) 1.3327(12) 0.1680(6) 0.067(5) Uiso 0.30 1 d PG A -2
H10C H 0.7964 1.3448 0.1937 0.080 Uiso 0.30 1 calc PR A -2
H10D H 0.8645 1.2927 0.0988 0.080 Uiso 0.30 1 calc PR A -2
C11A C 1.030(3) 1.4651(18) 0.1841(14) 0.067(5) Uiso 0.30 1 d PD A -2
H11C H 1.1322 1.4539 0.1587 0.080 Uiso 0.30 1 calc PR A -2
H11D H 1.0629 1.5064 0.2532 0.080 Uiso 0.30 1 calc PR A -2
C12A C 0.759(4) 1.609(5) 0.167(3) 0.143(13) Uiso 0.30 1 d PD A -2
H12D H 0.6839 1.5292 0.1794 0.214 Uiso 0.30 1 calc PR A -2
H12E H 0.6995 1.6331 0.1171 0.214 Uiso 0.30 1 calc PR A -2
H12F H 0.7925 1.6814 0.2250 0.214 Uiso 0.30 1 calc PR A -2
C13A C 1.106(6) 1.750(3) 0.158(5) 0.21(2) Uiso 0.30 1 d PD A -2
H13D H 1.0925 1.7896 0.1049 0.310 Uiso 0.30 1 calc PR A -2
H13E H 1.2226 1.7497 0.1688 0.310 Uiso 0.30 1 calc PR A -2
H13F H 1.0809 1.8025 0.2149 0.310 Uiso 0.30 1 calc PR A -2
C14A C 0.919(4) 1.509(3) -0.0037(12) 0.101(8) Uiso 0.30 1 d PD A -2
C9B C 0.9734(12) 1.2892(13) 0.2103(5) 0.116(13) Uiso 0.30 1 d PGD B -3
H9B1 H 1.0690 1.3053 0.1738 0.140 Uiso 0.30 1 calc PR A -3
H9B2 H 0.8916 1.2006 0.1783 0.140 Uiso 0.30 1 calc PR A -3
C10B C 0.892(2) 1.3834(19) 0.2068(13) 0.060(4) Uiso 0.30 1 d P B -3
H10E H 0.9738 1.4715 0.2404 0.071 Uiso 0.30 1 calc PR B -3
H10F H 0.7960 1.3660 0.2427 0.071 Uiso 0.30 1 calc PR B -3
C11B C 0.826(3) 1.390(2) 0.1119(17) 0.084(6) Uiso 0.30 1 d PD B -3
H11E H 0.7479 1.3011 0.0764 0.100 Uiso 0.30 1 calc PR B -3
H11F H 0.9223 1.4132 0.0768 0.100 Uiso 0.30 1 calc PR B -3
C12B C 0.516(3) 1.475(3) 0.177(2) 0.102(8) Uiso 0.30 1 d PD B -3
H12G H 0.4503 1.5320 0.1660 0.153 Uiso 0.30 1 calc PR B -3
H12H H 0.5520 1.4915 0.2449 0.153 Uiso 0.30 1 calc PR B -3
H12I H 0.4458 1.3824 0.1504 0.153 Uiso 0.30 1 calc PR B -3
C13B C 0.875(3) 1.676(2) 0.1719(19) 0.096(7) Uiso 0.30 1 d PD B -3
H13G H 0.8264 1.7461 0.1697 0.143 Uiso 0.30 1 calc PR B -3
H13H H 0.9718 1.6868 0.1370 0.143 Uiso 0.30 1 calc PR B -3
H13I H 0.9145 1.6818 0.2380 0.143 Uiso 0.30 1 calc PR B -3
C14B C 0.649(2) 1.5146(17) -0.0029(16) 0.104(8) Uiso 0.30 1 d PG B -3


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 S1 2.1464(11) 2_666 ?
Ni1 S1 2.1464(11) . ?
Ni1 S2 2.1665(11) . ?
Ni1 S2 2.1665(11) 2_666 ?
S1 C1 1.733(4) . ?
S2 C2 1.738(4) . ?
Si1 C12 1.85(2) . ?
Si1 C13 1.851(19) . ?
Si1 C11 1.85(2) . ?
Si1 C14 1.855(17) . ?
Si1A C14A 1.861(16) . ?
Si1A C11A 1.862(15) . ?
Si1A C13A 1.873(19) . ?
Si1A C12A 1.878(18) . ?
Si1B C14B 1.793(19) . ?
Si1B C13B 1.867(16) . ?
Si1B C11B 1.873(16) . ?
Si1B C12B 1.890(17) . ?
O1 C3 1.225(5) . ?
O2 C4 1.242(5) . ?
N1 C1 1.326(5) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N2 C2 1.326(5) . ?
N2 C1 1.342(5) . ?
N3 C2 1.331(5) . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
N4 C3 1.370(6) . ?
N4 C4 1.380(5) . ?
N4 H4 0.8800 . ?
N5 C7 1.365(5) . ?
N5 C3 1.376(6) . ?
N5 C8 1.470(5) . ?
C4 C5 1.440(6) . ?
C5 C7 1.342(6) . ?
C5 C6 1.497(6) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7 0.9500 . ?
C8 C9A 1.513(7) . ?
C8 C9B 1.514(7) . ?
C8 C9 1.558(10) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.47(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.44(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.3900 . ?
C14 C19 1.3900 . ?
C15 C16 1.3900 . ?
C15 H15 0.9500 . ?
C16 C17 1.3900 . ?
C16 H16 0.9500 . ?
C17 C18 1.3900 . ?
C17 H17 0.9500 . ?
C18 C19 1.3900 . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C9A C10A 1.3776 . ?
C9A H9A1 0.9900 . ?
C9A H9A2 0.9900 . ?
C10A C11A 1.49(2) . ?
C10A H10C 0.9900 . ?
C10A H10D 0.9900 . ?
C11A H11C 0.9900 . ?
C11A H11D 0.9900 . ?
C12A H12D 0.9800 . ?
C12A H12E 0.9800 . ?
C12A H12F 0.9800 . ?
C13A H13D 0.9800 . ?
C13A H13E 0.9800 . ?
C13A H13F 0.9800 . ?
C9B C10B 1.41(2) . ?
C9B H9B1 0.9900 . ?
C9B H9B2 0.9900 . ?
C10B C11B 1.48(3) . ?
C10B H10E 0.9900 . ?
C10B H10F 0.9900 . ?
C11B H11E 0.9900 . ?
C11B H11F 0.9900 . ?
C12B H12G 0.9800 . ?
C12B H12H 0.9800 . ?
C12B H12I 0.9800 . ?
C13B H13G 0.9800 . ?
C13B H13H 0.9800 . ?
C13B H13I 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
S1 Ni1 S1 180.00(4) 2_666 . ?
S1 Ni1 S2 85.29(4) 2_666 . ?
S1 Ni1 S2 94.71(4) . . ?
S1 Ni1 S2 94.71(4) 2_666 2_666 ?
S1 Ni1 S2 85.29(4) . 2_666 ?
S2 Ni1 S2 180.0 . 2_666 ?
C1 S1 Ni1 113.19(15) . . ?
C2 S2 Ni1 113.72(14) . . ?
C12 Si1 C13 113(2) . . ?
C12 Si1 C11 94(2) . . ?
C13 Si1 C11 112.9(17) . . ?
C12 Si1 C14 112(2) . . ?
C13 Si1 C14 111.9(12) . . ?
C11 Si1 C14 111.1(15) . . ?
C14A Si1A C11A 108.6(11) . . ?
C14A Si1A C13A 109(2) . . ?
C11A Si1A C13A 114(2) . . ?
C14A Si1A C12A 110.5(18) . . ?
C11A Si1A C12A 114.8(17) . . ?
C13A Si1A C12A 100(3) . . ?
C14B Si1B C13B 105.1(11) . . ?
C14B Si1B C11B 107.9(11) . . ?
C13B Si1B C11B 105.1(13) . . ?
C14B Si1B C12B 109.6(12) . . ?
C13B Si1B C12B 114.8(14) . . ?
C11B Si1B C12B 113.8(14) . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C2 N2 C1 124.7(3) . . ?
C2 N3 H3A 120.0 . . ?
C2 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C3 N4 C4 126.3(4) . . ?
C3 N4 H4 116.9 . . ?
C4 N4 H4 116.9 . . ?
C7 N5 C3 120.7(4) . . ?
C7 N5 C8 120.8(4) . . ?
C3 N5 C8 118.6(4) . . ?
N1 C1 N2 116.1(4) . . ?
N1 C1 S1 112.5(3) . . ?
N2 C1 S1 131.4(3) . . ?
N2 C2 N3 116.2(4) . . ?
N2 C2 S2 130.8(3) . . ?
N3 C2 S2 113.0(3) . . ?
O1 C3 N4 122.1(4) . . ?
O1 C3 N5 122.2(4) . . ?
N4 C3 N5 115.7(4) . . ?
O2 C4 N4 118.9(4) . . ?
O2 C4 C5 125.7(4) . . ?
N4 C4 C5 115.3(4) . . ?
C7 C5 C4 118.2(4) . . ?
C7 C5 C6 123.3(4) . . ?
C4 C5 C6 118.4(4) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 N5 123.8(4) . . ?
C5 C7 H7 118.1 . . ?
N5 C7 H7 118.1 . . ?
N5 C8 C9A 112.5(6) . . ?
N5 C8 C9B 126.0(7) . . ?
C9A C8 C9B 17.24(7) . . ?
N5 C8 C9 104.0(12) . . ?
C9A C8 C9 22.1(13) . . ?
C9B C8 C9 23.4(12) . . ?
N5 C8 H8A 110.9 . . ?
C9A C8 H8A 122.2 . . ?
C9B C8 H8A 105.1 . . ?
C9 C8 H8A 110.9 . . ?
N5 C8 H8B 110.9 . . ?
C9A C8 H8B 88.9 . . ?
C9B C8 H8B 92.9 . . ?
C9 C8 H8B 110.9 . . ?
H8A C8 H8B 109.0 . . ?
C10 C9 C8 135(3) . . ?
C10 C9 H9A 103.4 . . ?
C8 C9 H9A 103.4 . . ?
C10 C9 H9B 103.4 . . ?
C8 C9 H9B 103.4 . . ?
H9A C9 H9B 105.2 . . ?
C11 C10 C9 109(3) . . ?
C11 C10 H10A 109.9 . . ?
C9 C10 H10A 109.9 . . ?
C11 C10 H10B 109.9 . . ?
C9 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
C10 C11 Si1 124(3) . . ?
C10 C11 H11A 106.3 . . ?
Si1 C11 H11A 106.3 . . ?
C10 C11 H11B 106.3 . . ?
Si1 C11 H11B 106.3 . . ?
H11A C11 H11B 106.4 . . ?
Si1 C12 H12A 109.5 . . ?
Si1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
Si1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
Si1 C13 H13A 109.5 . . ?
Si1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
Si1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 120.0 . . ?
C15 C14 Si1 125.0(6) . . ?
C19 C14 Si1 115.0(6) . . ?
C14 C15 C16 120.0 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C17 120.0 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C18 C17 C16 120.0 . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 120.0 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C14 120.0 . . ?
C18 C19 H19 120.0 . . ?
C14 C19 H19 120.0 . . ?
C10A C9A C8 121.3(7) . . ?
C10A C9A H9A1 107.0 . . ?
C8 C9A H9A1 107.0 . . ?
C10A C9A H9A2 107.0 . . ?
C8 C9A H9A2 107.0 . . ?
H9A1 C9A H9A2 106.7 . . ?
C9A C10A C11A 115.0(8) . . ?
C9A C10A H10C 108.5 . . ?
C11A C10A H10C 108.5 . . ?
C9A C10A H10D 108.5 . . ?
C11A C10A H10D 108.5 . . ?
H10C C10A H10D 107.5 . . ?
C10A C11A Si1A 112.8(12) . . ?
C10A C11A H11C 109.0 . . ?
Si1A C11A H11C 109.0 . . ?
C10A C11A H11D 109.0 . . ?
Si1A C11A H11D 109.0 . . ?
H11C C11A H11D 107.8 . . ?
Si1A C12A H12D 109.5 . . ?
Si1A C12A H12E 109.5 . . ?
H12D C12A H12E 109.5 . . ?
Si1A C12A H12F 109.5 . . ?
H12D C12A H12F 109.5 . . ?
H12E C12A H12F 109.5 . . ?
Si1A C13A H13D 109.5 . . ?
Si1A C13A H13E 109.5 . . ?
H13D C13A H13E 109.5 . . ?
Si1A C13A H13F 109.5 . . ?
H13D C13A H13F 109.5 . . ?
H13E C13A H13F 109.5 . . ?
C10B C9B C8 115.2(10) . . ?
C10B C9B H9B1 108.5 . . ?
C8 C9B H9B1 108.5 . . ?
C10B C9B H9B2 108.5 . . ?
C8 C9B H9B2 108.5 . . ?
H9B1 C9B H9B2 107.5 . . ?
C9B C10B C11B 117.2(14) . . ?
C9B C10B H10E 108.0 . . ?
C11B C10B H10E 108.0 . . ?
C9B C10B H10F 108.0 . . ?
C11B C10B H10F 108.0 . . ?
H10E C10B H10F 107.3 . . ?
C10B C11B Si1B 113.2(15) . . ?
C10B C11B H11E 108.9 . . ?
Si1B C11B H11E 108.9 . . ?
C10B C11B H11F 108.9 . . ?
Si1B C11B H11F 108.9 . . ?
H11E C11B H11F 107.7 . . ?
Si1B C12B H12G 109.5 . . ?
Si1B C12B H12H 109.5 . . ?
H12G C12B H12H 109.5 . . ?
Si1B C12B H12I 109.5 . . ?
H12G C12B H12I 109.5 . . ?
H12H C12B H12I 109.5 . . ?
Si1B C13B H13G 109.5 . . ?
Si1B C13B H13H 109.5 . . ?
H13G C13B H13H 109.5 . . ?
Si1B C13B H13I 109.5 . . ?
H13G C13B H13I 109.5 . . ?
H13H C13B H13I 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 Ni1 S1 C1 -86(20) 2_666 . . . ?
S2 Ni1 S1 C1 -32.73(19) . . . . ?
S2 Ni1 S1 C1 147.27(19) 2_666 . . . ?
S1 Ni1 S2 C2 -148.44(19) 2_666 . . . ?
S1 Ni1 S2 C2 31.56(19) . . . . ?
S2 Ni1 S2 C2 64(8) 2_666 . . . ?
C2 N2 C1 N1 -176.4(4) . . . . ?
C2 N2 C1 S1 2.2(8) . . . . ?
Ni1 S1 C1 N1 -159.2(3) . . . . ?
Ni1 S1 C1 N2 22.2(5) . . . . ?
C1 N2 C2 N3 175.0(4) . . . . ?
C1 N2 C2 S2 -4.4(8) . . . . ?
Ni1 S2 C2 N2 -18.2(5) . . . . ?
Ni1 S2 C2 N3 162.4(3) . . . . ?
C4 N4 C3 O1 179.5(6) . . . . ?
C4 N4 C3 N5 0.8(8) . . . . ?
C7 N5 C3 O1 179.8(6) . . . . ?
C8 N5 C3 O1 -0.2(9) . . . . ?
C7 N5 C3 N4 -1.5(8) . . . . ?
C8 N5 C3 N4 178.5(5) . . . . ?
C3 N4 C4 O2 -179.0(5) . . . . ?
C3 N4 C4 C5 -0.1(8) . . . . ?
O2 C4 C5 C7 178.9(5) . . . . ?
N4 C4 C5 C7 0.0(7) . . . . ?
O2 C4 C5 C6 -2.6(8) . . . . ?
N4 C4 C5 C6 178.6(5) . . . . ?
C4 C5 C7 N5 -0.8(8) . . . . ?
C6 C5 C7 N5 -179.2(5) . . . . ?
C3 N5 C7 C5 1.6(8) . . . . ?
C8 N5 C7 C5 -178.5(5) . . . . ?
C7 N5 C8 C9A 102.0(7) . . . . ?
C3 N5 C8 C9A -78.0(7) . . . . ?
C7 N5 C8 C9B 89.6(8) . . . . ?
C3 N5 C8 C9B -90.4(8) . . . . ?
C7 N5 C8 C9 80.5(13) . . . . ?
C3 N5 C8 C9 -99.5(13) . . . . ?
N5 C8 C9 C10 51(4) . . . . ?
C9A C8 C9 C10 -65(5) . . . . ?
C9B C8 C9 C10 -110(6) . . . . ?
C8 C9 C10 C11 84(5) . . . . ?
C9 C10 C11 Si1 -167(3) . . . . ?
C12 Si1 C11 C10 49(4) . . . . ?
C13 Si1 C11 C10 -68(4) . . . . ?
C14 Si1 C11 C10 165(3) . . . . ?
C12 Si1 C14 C15 1(2) . . . . ?
C13 Si1 C14 C15 129.6(11) . . . . ?
C11 Si1 C14 C15 -103.3(16) . . . . ?
C12 Si1 C14 C19 -180(2) . . . . ?
C13 Si1 C14 C19 -51.3(12) . . . . ?
C11 Si1 C14 C19 75.8(16) . . . . ?
C19 C14 C15 C16 0.0 . . . . ?
Si1 C14 C15 C16 179.0(5) . . . . ?
C14 C15 C16 C17 0.0 . . . . ?
C15 C16 C17 C18 0.0 . . . . ?
C16 C17 C18 C19 0.0 . . . . ?
C17 C18 C19 C14 0.0 . . . . ?
C15 C14 C19 C18 0.0 . . . . ?
Si1 C14 C19 C18 -179.1(5) . . . . ?
N5 C8 C9A C10A -171.4(4) . . . . ?
C9B C8 C9A C10A -27.3(4) . . . . ?
C9 C8 C9A C10A -100(3) . . . . ?
C8 C9A C10A C11A 45.3(11) . . . . ?
C9A C10A C11A Si1A 179.5(8) . . . . ?
C14A Si1A C11A C10A -65.7(17) . . . . ?
C13A Si1A C11A C10A 173(2) . . . . ?
C12A Si1A C11A C10A 58(2) . . . . ?
N5 C8 C9B C10B 169.3(11) . . . . ?
C9A C8 C9B C10B 127.3(12) . . . . ?
C9 C8 C9B C10B -168(4) . . . . ?
C8 C9B C10B C11B 178.9(15) . . . . ?
C9B C10B C11B Si1B 176.8(15) . . . . ?
C14B Si1B C11B C10B 176.8(16) . . . . ?
C13B Si1B C11B C10B 65(2) . . . . ?
C12B Si1B C11B C10B -61(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         1.126
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.086
_database_code_depnum_ccdc_archive 'CCDC 956091'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Compound-19-h06kcm6

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H31 N2 O3 Si2'
_chemical_formula_sum            'C17 H31 N2 O3 Si2'
_chemical_formula_weight         367.62

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6867(3)
_cell_length_b                   8.6444(4)
_cell_length_c                   17.9501(11)
_cell_angle_alpha                85.273(2)
_cell_angle_beta                 79.127(2)
_cell_angle_gamma                64.283(2)
_cell_volume                     1055.30(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    16111
_cell_measurement_theta_min      2.910
_cell_measurement_theta_max      25.350

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.157
_exptl_crystal_F_000             398
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.184
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.937
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       '181 1.8 degree images with φ and ω scans'
_diffrn_reflns_number            11515
_diffrn_reflns_av_unetI/netI     0.0668
_diffrn_reflns_av_R_equivalents  0.0632
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         5.727
_diffrn_reflns_theta_max         25.530
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             3796
_reflns_number_gt                2589
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
;
 DENZO-SCALEPACK Z. Otwinowski and W. Minor, " 
 Processing of X-ray Diffraction Data Collected in Oscillation Mode ", 
 Methods in Enzymology, Volume 276: Macromolecular Crystallography, 
 part A, p.307-326, 1997,C.W. Carter, Jr. & R. M. Sweet, Eds., Academic Press.
;
_computing_structure_solution    
; 
 SIR97- Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C. , 
 Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. 
 (1999) J. Appl. Cryst. 32, 115-119
;
_computing_structure_refinement  
;
 SHELXL-2012 (Sheldrick, 2012)
 Sheldrick GM (2008) Acta Crystallogr A64:112--122 and 
 C. B. Hübschle, G. M. Sheldrick and B. Dittrich
 ShelXle: a Qt graphical user interface for SHELXL
 J. Appl. Cryst., 44, (2011) 1281-1284.
;
_computing_molecular_graphics    
'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565'

_computing_publication_material  
;
 'WinGX publication routines, Farrugia, 
 L. J., J. Appl. Crystallogr., 1999, 32, 837-838
;

_refine_special_details          
;
 O3 and O3A have 50% occupation
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0530P)²+0.7787P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.101(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3796
_refine_ls_number_parameters     232
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0943
_refine_ls_R_factor_gt           0.0593
_refine_ls_wR_factor_ref         0.1528
_refine_ls_wR_factor_gt          0.1324
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.12718(18) 0.38174(12) 0.14885(6) 0.0625(4) Uani 1 1 d . . . . .
Si2 Si 0.01103(16) 0.77752(12) 0.15555(5) 0.0576(3) Uani 1 1 d . . . . .
O1 O 0.0663(3) 0.5761(3) 0.17548(12) 0.0514(6) Uani 1 1 d . . . . .
O2 O 0.5466(3) 0.5018(3) 0.33409(11) 0.0450(5) Uani 1 1 d . . . . .
O3 O 0.3400(8) 0.1762(6) 0.5094(3) 0.0634(13) Uani 0.5 1 d . . P . .
O3A O 0.0712(7) 0.7607(6) 0.5383(3) 0.0612(12) Uani 0.5 1 d . . P . .
N1 N 0.4445(3) 0.3370(3) 0.42057(13) 0.0392(6) Uani 1 1 d . . . . .
N2 N 0.3136(3) 0.6335(3) 0.43595(13) 0.0394(6) Uani 1 1 d . . . . .
C1 C -0.0930(9) 0.3666(6) 0.1288(3) 0.117(2) Uani 1 1 d . . . . .
H1A H -0.1927 0.3948 0.1748 0.175 Uiso 1 1 calc R U . . .
H1B H -0.0572 0.2495 0.1127 0.175 Uiso 1 1 calc R U . . .
H1C H -0.1453 0.4475 0.0884 0.175 Uiso 1 1 calc R U . . .
C2 C 0.3195(9) 0.3272(6) 0.0654(2) 0.112(2) Uani 1 1 d . . . . .
H2A H 0.2667 0.3983 0.0224 0.167 Uiso 1 1 calc R U . . .
H2B H 0.3671 0.2057 0.0529 0.167 Uiso 1 1 calc R U . . .
H2C H 0.4279 0.3482 0.0759 0.167 Uiso 1 1 calc R U . . .
C3 C 0.2081(10) 0.7967(7) 0.0850(3) 0.116(2) Uani 1 1 d . . . . .
H3A H 0.3321 0.7408 0.1044 0.175 Uiso 1 1 calc R U . . .
H3B H 0.1771 0.9184 0.0754 0.175 Uiso 1 1 calc R U . . .
H3C H 0.2201 0.7412 0.0377 0.175 Uiso 1 1 calc R U . . .
C4 C -0.2214(9) 0.8758(6) 0.1182(3) 0.119(2) Uani 1 1 d . . . . .
H4A H -0.2037 0.8233 0.0693 0.179 Uiso 1 1 calc R U . . .
H4B H -0.2605 0.9994 0.1112 0.179 Uiso 1 1 calc R U . . .
H4C H -0.3234 0.8571 0.1541 0.179 Uiso 1 1 calc R U . . .
C5 C 0.2196(6) 0.2347(4) 0.2279(2) 0.0581(9) Uani 1 1 d . . . . .
H5A H 0.1066 0.2471 0.2680 0.070 Uiso 1 1 calc R U . . .
H5B H 0.2803 0.1152 0.2090 0.070 Uiso 1 1 calc R U . . .
C6 C 0.3699(5) 0.2632(4) 0.26376(17) 0.0489(8) Uani 1 1 d . . . . .
H6A H 0.4848 0.2485 0.2242 0.059 Uiso 1 1 calc R U . . .
H6B H 0.3107 0.3828 0.2826 0.059 Uiso 1 1 calc R U . . .
C7 C 0.4390(5) 0.1402(4) 0.32932(18) 0.0496(8) Uani 1 1 d . . . . .
H7A H 0.3227 0.1419 0.3648 0.060 Uiso 1 1 calc R U . . .
H7B H 0.5155 0.0222 0.3089 0.060 Uiso 1 1 calc R U . . .
C8 C 0.5643(5) 0.1823(4) 0.37339(18) 0.0466(7) Uani 1 1 d . . . . .
H8A H 0.6290 0.0839 0.4062 0.056 Uiso 1 1 calc R U . . .
H8B H 0.6678 0.2014 0.3374 0.056 Uiso 1 1 calc R U . . .
C9 C 0.4427(4) 0.4919(4) 0.39287(16) 0.0381(6) Uani 1 1 d . . . . .
C10 C 0.3343(5) 0.3204(4) 0.48912(17) 0.0466(7) Uani 1 1 d . . . . .
C11 C 0.2129(5) 0.4656(4) 0.53240(16) 0.0473(8) Uani 1 1 d . . . . .
C12 C 0.0991(6) 0.4496(6) 0.60827(18) 0.0699(11) Uani 1 1 d . . . . .
H12A H 0.0901 0.3395 0.6110 0.105 Uiso 1 1 calc R U . . .
H12B H -0.0330 0.5437 0.6146 0.105 Uiso 1 1 calc R U . . .
H12C H 0.1661 0.4550 0.6487 0.105 Uiso 1 1 calc R U . . .
C13 C 0.1983(5) 0.6244(4) 0.50451(17) 0.0473(8) Uani 1 1 d . . . . .
C14 C 0.2906(5) 0.8054(4) 0.40712(19) 0.0490(8) Uani 1 1 d . . . . .
H14A H 0.4131 0.7947 0.3735 0.059 Uiso 1 1 calc R U . . .
H14B H 0.2682 0.8796 0.4504 0.059 Uiso 1 1 calc R U . . .
C15 C 0.1205(5) 0.8899(4) 0.36340(18) 0.0508(8) Uani 1 1 d . . . . .
H15A H 0.0938 1.0122 0.3549 0.061 Uiso 1 1 calc R U . . .
H15B H 0.0020 0.8859 0.3949 0.061 Uiso 1 1 calc R U . . .
C16 C 0.1570(5) 0.8057(4) 0.28660(17) 0.0467(7) Uani 1 1 d . . . . .
H16A H 0.2712 0.8152 0.2540 0.056 Uiso 1 1 calc R U . . .
H16B H 0.1901 0.6821 0.2947 0.056 Uiso 1 1 calc R U . . .
C17 C -0.0181(5) 0.8859(4) 0.24551(18) 0.0538(8) Uani 1 1 d . . . . .
H17A H -0.0441 1.0072 0.2341 0.065 Uiso 1 1 calc R U . . .
H17B H -0.1345 0.8853 0.2801 0.065 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Si1 O1 1.623(2) . ?
Si1 C2 1.824(5) . ?
Si1 C5 1.853(3) . ?
Si1 C1 1.855(5) . ?
Si2 O1 1.629(2) . ?
Si2 C3 1.840(5) . ?
Si2 C4 1.845(5) . ?
Si2 C17 1.862(3) . ?
O2 C9 1.219(3) . ?
O3 C10 1.254(5) . ?
O3A C13 1.267(5) . ?
N1 C9 1.385(3) . ?
N1 C10 1.391(4) . ?
N1 C8 1.475(4) . ?
N2 C9 1.376(4) . ?
N2 C13 1.393(4) . ?
N2 C14 1.479(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.537(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.529(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.525(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C10 C11 1.386(5) . ?
C11 C13 1.386(4) . ?
C11 C12 1.504(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C14 C15 1.524(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.533(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.522(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Si1 C2 109.5(2) . . ?
O1 Si1 C5 107.96(13) . . ?
C2 Si1 C5 109.7(2) . . ?
O1 Si1 C1 109.1(2) . . ?
C2 Si1 C1 111.3(3) . . ?
C5 Si1 C1 109.23(19) . . ?
O1 Si2 C3 110.0(2) . . ?
O1 Si2 C4 109.9(2) . . ?
C3 Si2 C4 109.8(3) . . ?
O1 Si2 C17 107.19(13) . . ?
C3 Si2 C17 110.3(2) . . ?
C4 Si2 C17 109.56(19) . . ?
Si1 O1 Si2 150.53(15) . . ?
C9 N1 C10 123.6(2) . . ?
C9 N1 C8 118.1(2) . . ?
C10 N1 C8 118.3(2) . . ?
C9 N2 C13 123.5(2) . . ?
C9 N2 C14 118.6(2) . . ?
C13 N2 C14 117.9(2) . . ?
Si1 C1 H1A 109.5 . . ?
Si1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
Si1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
Si1 C2 H2A 109.5 . . ?
Si1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
Si1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
Si2 C3 H3A 109.5 . . ?
Si2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
Si2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
Si2 C4 H4A 109.5 . . ?
Si2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
Si2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 Si1 115.3(2) . . ?
C6 C5 H5A 108.5 . . ?
Si1 C5 H5A 108.5 . . ?
C6 C5 H5B 108.5 . . ?
Si1 C5 H5B 108.5 . . ?
H5A C5 H5B 107.5 . . ?
C7 C6 C5 113.0(3) . . ?
C7 C6 H6A 109.0 . . ?
C5 C6 H6A 109.0 . . ?
C7 C6 H6B 109.0 . . ?
C5 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C8 C7 C6 114.1(3) . . ?
C8 C7 H7A 108.7 . . ?
C6 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
C6 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
N1 C8 C7 111.2(2) . . ?
N1 C8 H8A 109.4 . . ?
C7 C8 H8A 109.4 . . ?
N1 C8 H8B 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
O2 C9 N2 122.6(2) . . ?
O2 C9 N1 122.2(3) . . ?
N2 C9 N1 115.2(2) . . ?
O3 C10 C11 121.0(4) . . ?
O3 C10 N1 119.8(4) . . ?
C11 C10 N1 119.2(3) . . ?
C13 C11 C10 118.9(3) . . ?
C13 C11 C12 121.0(3) . . ?
C10 C11 C12 120.0(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O3A C13 C11 120.2(4) . . ?
O3A C13 N2 120.2(4) . . ?
C11 C13 N2 119.4(3) . . ?
N2 C14 C15 112.2(2) . . ?
N2 C14 H14A 109.2 . . ?
C15 C14 H14A 109.2 . . ?
N2 C14 H14B 109.2 . . ?
C15 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C14 C15 C16 113.9(3) . . ?
C14 C15 H15A 108.8 . . ?
C16 C15 H15A 108.8 . . ?
C14 C15 H15B 108.8 . . ?
C16 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
C17 C16 C15 113.2(3) . . ?
C17 C16 H16A 108.9 . . ?
C15 C16 H16A 108.9 . . ?
C17 C16 H16B 108.9 . . ?
C15 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
C16 C17 Si2 115.0(2) . . ?
C16 C17 H17A 108.5 . . ?
Si2 C17 H17A 108.5 . . ?
C16 C17 H17B 108.5 . . ?
Si2 C17 H17B 108.5 . . ?
H17A C17 H17B 107.5 . . ?

_refine_diff_density_max         0.265
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.045

_shelxl_version_number           2013-3

_database_code_depnum_ccdc_archive 'CCDC 956092'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Compound-21-k06kcm4

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H32 N3 O2 Si2'
_chemical_formula_sum            'C16 H32 N3 O2 Si2'
_chemical_formula_weight         354.62

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1751(2)
_cell_length_b                   8.9309(3)
_cell_length_c                   15.8082(5)
_cell_angle_alpha                96.0320(10)
_cell_angle_beta                 96.8080(10)
_cell_angle_gamma                95.324(2)
_cell_volume                     994.58(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    27949
_cell_measurement_theta_min      2.910
_cell_measurement_theta_max      27.485

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_F_000             386
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.191
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       '376 1.5 degree images with φ and ω scans'
_diffrn_reflns_number            15784
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.277
_diffrn_reflns_theta_max         27.529
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4534
_reflns_number_gt                3722
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
;
 DENZO-SCALEPACK Z. Otwinowski and W. Minor, " 
 Processing of X-ray Diffraction Data Collected in Oscillation Mode ", 
 Methods in Enzymology, Volume 276: Macromolecular Crystallography, 
 part A, p.307-326, 1997,C.W. Carter, Jr. & R. M. Sweet, Eds., Academic Press.
;
_computing_structure_solution    
; 
 SIR97- Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C. , 
 Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. 
 (1999) J. Appl. Cryst. 32, 115-119
;
_computing_structure_refinement  
;
 SHELXL-2013 (Sheldrick, 2013)
 Sheldrick GM (2008) Acta Crystallogr A64:112--122 and 
 C. B. Hübschle, G. M. Sheldrick and B. Dittrich
 ShelXle: a Qt graphical user interface for SHELXL
 J. Appl. Cryst., 44, (2011) 1281-1284.
;
_computing_molecular_graphics    
'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565'

_computing_publication_material  
;
 'WinGX publication routines, Farrugia, 
 L. J., J. Appl. Crystallogr., 1999, 32, 837-838
;

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0327P)²+0.6368P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4534
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0555
_refine_ls_wR_factor_ref         0.1156
_refine_ls_wR_factor_gt          0.1087
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_restrained_S_all      1.107
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si -0.18105(8) 0.20991(6) 0.08669(3) 0.02904(15) Uani 1 1 d . . . . .
Si2 Si -0.21273(8) -0.06301(6) 0.19817(4) 0.03384(16) Uani 1 1 d . . . . .
O1 O -0.13813(19) 0.07510(15) 0.14608(9) 0.0334(3) Uani 1 1 d . . . . .
O2 O 0.10205(18) 0.41666(17) 0.40755(9) 0.0384(4) Uani 1 1 d . . . . .
C1 C -0.3942(3) 0.2973(3) 0.11526(15) 0.0443(6) Uani 1 1 d . . . . .
H1A H -0.4163 0.3802 0.0806 0.066 Uiso 1 1 calc R U . . .
H1B H -0.3746 0.3370 0.1762 0.066 Uiso 1 1 calc R U . . .
H1C H -0.5040 0.2208 0.1040 0.066 Uiso 1 1 calc R U . . .
C2 C -0.2224(3) 0.1283(3) -0.02796(13) 0.0425(5) Uani 1 1 d . . . . .
H2A H -0.2439 0.2091 -0.0642 0.064 Uiso 1 1 calc R U . . .
H2B H -0.3334 0.0529 -0.0373 0.064 Uiso 1 1 calc R U . . .
H2C H -0.1116 0.0797 -0.0427 0.064 Uiso 1 1 calc R U . . .
C3 C 0.0277(3) 0.3566(2) 0.10714(13) 0.0355(5) Uani 1 1 d . . . . .
H3A H 0.1371 0.3124 0.0856 0.043 Uiso 1 1 calc R U . . .
H3B H 0.0001 0.4422 0.0743 0.043 Uiso 1 1 calc R U . . .
C4 C 0.0811(3) 0.4171(2) 0.20202(13) 0.0382(5) Uani 1 1 d . . . . .
H4A H -0.0325 0.4512 0.2249 0.046 Uiso 1 1 calc R U . . .
H4B H 0.1208 0.3330 0.2337 0.046 Uiso 1 1 calc R U . . .
C5 C 0.2388(4) 0.5479(3) 0.21982(15) 0.0460(6) Uani 1 1 d . . . . .
H5A H 0.1945 0.6356 0.1929 0.055 Uiso 1 1 calc R U . A 1
H5B H 0.3485 0.5173 0.1923 0.055 Uiso 1 1 calc R U . A 1
N2 N 0.6804(4) 0.5662(3) 0.33065(17) 0.0404(8) Uani 0.698(5) 1 d . . P B 1
H2D H 0.6253 0.6341 0.3030 0.048 Uiso 0.698(5) 1 calc R U P B 1
H2E H 0.8027 0.5617 0.3318 0.048 Uiso 0.698(5) 1 calc R U P B 1
C6 C 0.3041(8) 0.5982(5) 0.3161(3) 0.0350(11) Uani 0.698(5) 1 d . . P B 1
H6A H 0.3995 0.6872 0.3210 0.042 Uiso 0.698(5) 1 calc R U P B 1
H6B H 0.1946 0.6317 0.3427 0.042 Uiso 0.698(5) 1 calc R U P B 1
N1 N 0.3861(5) 0.4830(5) 0.3666(2) 0.0252(8) Uani 0.698(5) 1 d . . P B 1
N3 N 0.3478(8) 0.2849(6) 0.4506(3) 0.0350(10) Uani 0.698(5) 1 d . . P B 1
C7 C 0.5834(5) 0.4747(5) 0.3689(2) 0.0242(7) Uani 0.698(5) 1 d . . P B 1
C8 C 0.6554(5) 0.3608(5) 0.4161(2) 0.0283(8) Uani 0.698(5) 1 d . . P B 1
H8 H 0.7863 0.3486 0.4215 0.034 Uiso 0.698(5) 1 calc R U P B 1
C9 C 0.5372(5) 0.2711(4) 0.4530(2) 0.0289(8) Uani 0.698(5) 1 d . . P B 1
H9 H 0.5873 0.1934 0.4825 0.035 Uiso 0.698(5) 1 calc R U P B 1
C10 C 0.2660(7) 0.3936(6) 0.4102(3) 0.0265(11) Uani 0.698(5) 1 d . . P B 1
N2A N 0.6551(14) 0.2175(10) 0.4709(5) 0.071(3) Uiso 0.302(5) 1 d . . P B 2
H2F H 0.7762 0.2080 0.4715 0.085 Uiso 0.302(5) 1 calc R U P B 2
H2G H 0.5847 0.1564 0.4974 0.085 Uiso 0.302(5) 1 calc R U P B 2
C6A C 0.2562(19) 0.6203(18) 0.3141(10) 0.044(4) Uiso 0.302(5) 1 d . . P B 2
H6C H 0.3228 0.7239 0.3224 0.053 Uiso 0.302(5) 1 calc R U P B 2
H6D H 0.1318 0.6219 0.3352 0.053 Uiso 0.302(5) 1 calc R U P B 2
N1A N 0.3659(15) 0.5161(12) 0.3528(6) 0.026(3) Uiso 0.302(5) 1 d . . P B 2
N3A N 0.372(2) 0.3076(16) 0.4368(9) 0.034(3) Uiso 0.302(5) 1 d . . P B 2
C7A C 0.5553(14) 0.5199(11) 0.3506(6) 0.031(3) Uiso 0.302(5) 1 d . . P B 2
H7A H 0.6165 0.5940 0.3214 0.037 Uiso 0.302(5) 1 calc R U P B 2
C8A C 0.6540(14) 0.4247(13) 0.3873(7) 0.035(2) Uiso 0.302(5) 1 d . . P B 2
H8A H 0.7850 0.4307 0.3822 0.042 Uiso 0.302(5) 1 calc R U P B 2
C9A C 0.5830(16) 0.3175(13) 0.4325(6) 0.030(2) Uiso 0.302(5) 1 d . . P B 2
C10A C 0.2756(19) 0.4211(13) 0.3965(8) 0.016(3) Uiso 0.302(5) 1 d . . P B 2
C11 C 0.2371(4) 0.1801(3) 0.48532(15) 0.0586(7) Uani 1 1 d . . . . .
H11A H 0.1219 0.2245 0.5001 0.070 Uiso 1 1 calc R U . B 1
H11B H 0.3069 0.1549 0.5389 0.070 Uiso 1 1 calc R U . B 1
C12 C 0.1803(4) 0.0357(3) 0.42362(15) 0.0561(7) Uani 1 1 d . . . . .
H12A H 0.2944 0.0010 0.4015 0.067 Uiso 1 1 calc R U . . .
H12B H 0.1268 -0.0444 0.4553 0.067 Uiso 1 1 calc R U . . .
C13 C 0.0366(4) 0.0572(3) 0.34841(14) 0.0482(6) Uani 1 1 d . . . . .
H13A H 0.0897 0.1388 0.3176 0.058 Uiso 1 1 calc R U . . .
H13B H -0.0778 0.0907 0.3708 0.058 Uiso 1 1 calc R U . . .
C14 C -0.0207(4) -0.0855(2) 0.28464(14) 0.0426(5) Uani 1 1 d . . . . .
H14A H -0.0628 -0.1697 0.3163 0.051 Uiso 1 1 calc R U . . .
H14B H 0.0913 -0.1134 0.2581 0.051 Uiso 1 1 calc R U . . .
C15 C -0.4269(3) -0.0156(3) 0.24694(16) 0.0505(6) Uani 1 1 d . . . . .
H15A H -0.5318 -0.0140 0.2014 0.076 Uiso 1 1 calc R U . . .
H15B H -0.4009 0.0842 0.2808 0.076 Uiso 1 1 calc R U . . .
H15C H -0.4606 -0.0920 0.2843 0.076 Uiso 1 1 calc R U . . .
C16 C -0.2668(4) -0.2424(3) 0.12468(15) 0.0471(6) Uani 1 1 d . . . . .
H16A H -0.3612 -0.2285 0.0768 0.071 Uiso 1 1 calc R U . . .
H16B H -0.3165 -0.3230 0.1560 0.071 Uiso 1 1 calc R U . . .
H16C H -0.1513 -0.2702 0.1025 0.071 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Si1 O1 1.6321(15) . ?
Si1 C2 1.860(2) . ?
Si1 C1 1.861(2) . ?
Si1 C3 1.870(2) . ?
Si2 O1 1.6375(15) . ?
Si2 C16 1.858(2) . ?
Si2 C15 1.862(2) . ?
Si2 C14 1.862(2) . ?
O2 C10 1.210(6) . ?
O2 C10A 1.276(14) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.531(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.528(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.544(5) . ?
C5 C6A 1.547(15) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
N2 C7 1.272(4) . ?
N2 H2D 0.8800 . ?
N2 H2E 0.8800 . ?
C6 N1 1.489(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
N1 C10 1.408(6) . ?
N1 C7 1.421(5) . ?
N3 C10 1.358(8) . ?
N3 C11 1.371(6) . ?
N3 C9 1.372(6) . ?
C7 C8 1.423(5) . ?
C8 C9 1.337(5) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
N2A C9A 1.249(13) . ?
N2A H2F 0.8800 . ?
N2A H2G 0.8800 . ?
C6A N1A 1.414(14) . ?
C6A H6C 0.9900 . ?
C6A H6D 0.9900 . ?
N1A C10A 1.321(14) . ?
N1A C7A 1.361(15) . ?
N3A C10A 1.441(19) . ?
N3A C9A 1.517(18) . ?
N3A C11 1.726(12) . ?
C7A C8A 1.296(13) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.351(14) . ?
C8A H8A 0.9500 . ?
C11 C12 1.525(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.519(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.531(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Si1 C2 108.94(9) . . ?
O1 Si1 C1 110.14(10) . . ?
C2 Si1 C1 109.33(11) . . ?
O1 Si1 C3 108.12(9) . . ?
C2 Si1 C3 110.90(10) . . ?
C1 Si1 C3 109.40(10) . . ?
O1 Si2 C16 110.29(10) . . ?
O1 Si2 C15 109.98(10) . . ?
C16 Si2 C15 110.04(11) . . ?
O1 Si2 C14 107.75(9) . . ?
C16 Si2 C14 109.33(11) . . ?
C15 Si2 C14 109.40(12) . . ?
Si1 O1 Si2 150.42(10) . . ?
Si1 C1 H1A 109.5 . . ?
Si1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
Si1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
Si1 C2 H2A 109.5 . . ?
Si1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
Si1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 Si1 113.45(14) . . ?
C4 C3 H3A 108.9 . . ?
Si1 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
Si1 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C5 C4 C3 114.62(18) . . ?
C5 C4 H4A 108.6 . . ?
C3 C4 H4A 108.6 . . ?
C5 C4 H4B 108.6 . . ?
C3 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?
C4 C5 C6 114.2(2) . . ?
C4 C5 C6A 110.5(6) . . ?
C4 C5 H5A 108.7 . . ?
C6 C5 H5A 108.7 . . ?
C4 C5 H5B 108.7 . . ?
C6 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
C7 N2 H2D 120.0 . . ?
C7 N2 H2E 120.0 . . ?
H2D N2 H2E 120.0 . . ?
N1 C6 C5 116.5(3) . . ?
N1 C6 H6A 108.2 . . ?
C5 C6 H6A 108.2 . . ?
N1 C6 H6B 108.2 . . ?
C5 C6 H6B 108.2 . . ?
H6A C6 H6B 107.3 . . ?
C10 N1 C7 124.8(4) . . ?
C10 N1 C6 118.5(4) . . ?
C7 N1 C6 116.7(4) . . ?
C10 N3 C11 119.3(4) . . ?
C10 N3 C9 121.6(5) . . ?
C11 N3 C9 118.9(5) . . ?
N2 C7 N1 119.6(5) . . ?
N2 C7 C8 125.5(4) . . ?
N1 C7 C8 115.0(3) . . ?
C9 C8 C7 119.4(3) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 N3 123.8(4) . . ?
C8 C9 H9 118.1 . . ?
N3 C9 H9 118.1 . . ?
O2 C10 N3 125.8(4) . . ?
O2 C10 N1 118.9(5) . . ?
N3 C10 N1 115.3(5) . . ?
C9A N2A H2F 120.0 . . ?
C9A N2A H2G 120.0 . . ?
H2F N2A H2G 120.0 . . ?
N1A C6A C5 98.6(9) . . ?
N1A C6A H6C 112.0 . . ?
C5 C6A H6C 112.0 . . ?
N1A C6A H6D 112.0 . . ?
C5 C6A H6D 112.0 . . ?
H6C C6A H6D 109.7 . . ?
C10A N1A C7A 121.6(10) . . ?
C10A N1A C6A 115.8(12) . . ?
C7A N1A C6A 122.4(11) . . ?
C10A N3A C9A 115.1(10) . . ?
C10A N3A C11 116.8(10) . . ?
C9A N3A C11 128.1(10) . . ?
C8A C7A N1A 121.6(10) . . ?
C8A C7A H7A 119.2 . . ?
N1A C7A H7A 119.2 . . ?
C7A C8A C9A 124.3(10) . . ?
C7A C8A H8A 117.8 . . ?
C9A C8A H8A 117.8 . . ?
N2A C9A C8A 133.0(12) . . ?
N2A C9A N3A 110.5(12) . . ?
C8A C9A N3A 116.4(9) . . ?
O2 C10A N1A 126.1(10) . . ?
O2 C10A N3A 113.3(9) . . ?
N1A C10A N3A 120.6(12) . . ?
N3 C11 C12 111.8(3) . . ?
C12 C11 N3A 109.3(5) . . ?
N3 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
N3 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C13 C12 C11 112.8(2) . . ?
C13 C12 H12A 109.0 . . ?
C11 C12 H12A 109.0 . . ?
C13 C12 H12B 109.0 . . ?
C11 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C12 C13 C14 113.9(2) . . ?
C12 C13 H13A 108.8 . . ?
C14 C13 H13A 108.8 . . ?
C12 C13 H13B 108.8 . . ?
C14 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C13 C14 Si2 113.59(16) . . ?
C13 C14 H14A 108.8 . . ?
Si2 C14 H14A 108.8 . . ?
C13 C14 H14B 108.8 . . ?
Si2 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
Si2 C15 H15A 109.5 . . ?
Si2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
Si2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
Si2 C16 H16A 109.5 . . ?
Si2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
Si2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H8 O2 0.95 2.33 3.218(4) 154.8 1_655
C12 H12B N2A 0.99 2.57 3.179(9) 119.9 2_656

_refine_diff_density_max         0.370
_refine_diff_density_min         -0.619
_refine_diff_density_rms         0.133

_shelxl_version_number           2013-3

_database_code_depnum_ccdc_archive 'CCDC 956093'
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#                                CCDC 
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#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
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#  except for the purpose of generating routine backup copies
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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data_Compound-9a-h06kcm16

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H8 N6 Ni S4, 2(C5 H6 N2 O2)'
_chemical_formula_sum            'C14 H20 N10 Ni O4 S4'
_chemical_formula_weight         579.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5968(5)
_cell_length_b                   8.2841(5)
_cell_length_c                   9.0845(6)
_cell_angle_alpha                104.418(3)
_cell_angle_beta                 98.826(3)
_cell_angle_gamma                95.465(3)
_cell_volume                     541.80(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    14302
_cell_measurement_theta_min      2.910
_cell_measurement_theta_max      27.485

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.776
_exptl_crystal_F_000             298
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    1.328
_shelx_estimated_absorpt_T_min   0.691
_shelx_estimated_absorpt_T_max   0.937
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.791
_exptl_absorpt_correction_T_max  0.941
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       '176 2.0 degree images with ω scans'
_diffrn_reflns_number            7488
_diffrn_reflns_av_unetI/netI     0.0559
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         7.434
_diffrn_reflns_theta_max         27.535
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.968
_reflns_number_total             2425
_reflns_number_gt                1994
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
;
 DENZO-SCALEPACK Z. Otwinowski and W. Minor, " 
 Processing of X-ray Diffraction Data Collected in Oscillation Mode ", 
 Methods in Enzymology, Volume 276: Macromolecular Crystallography, 
 part A, p.307-326, 1997,C.W. Carter, Jr. & R. M. Sweet, Eds., Academic Press.
;
_computing_structure_solution    
; 
 SIR97- Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C. , 
 Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. 
 (1999) J. Appl. Cryst. 32, 115-119
;
_computing_structure_refinement  
;
 SHELXL-2012 (Sheldrick, 2012)
 Sheldrick GM (2008) Acta Crystallogr A64:112--122 and 
 C. B. Hübschle, G. M. Sheldrick and B. Dittrich
 ShelXle: a Qt graphical user interface for SHELXL
 J. Appl. Cryst., 44, (2011) 1281-1284.
;
_computing_molecular_graphics    
'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565'

_computing_publication_material  
;
 'WinGX publication routines, Farrugia, 
 L. J., J. Appl. Crystallogr., 1999, 32, 837-838
;

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0424P)²+0.7622P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2425
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1186
_refine_ls_wR_factor_gt          0.1099
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni Ni 0.5000 0.5000 0.5000 0.02445(18) Uani 1 2 d S . P . .
S1 S 0.47064(12) 0.76475(10) 0.55407(9) 0.0307(2) Uani 1 1 d . . . . .
S2 S 0.51549(12) 0.48487(10) 0.73485(9) 0.0284(2) Uani 1 1 d . . . . .
N1 N 0.5755(5) 1.0460(4) 0.7619(4) 0.0375(7) Uani 1 1 d . . . . .
H1A H 0.554(6) 1.089(6) 0.677(5) 0.039(11) Uiso 1 1 d . . . . .
H1B H 0.634(7) 1.121(7) 0.854(7) 0.053(13) Uiso 1 1 d . . . . .
C1 C 0.5668(5) 0.8804(4) 0.7416(4) 0.0280(6) Uani 1 1 d . . . . .
N2 N 0.6328(4) 0.8311(3) 0.8654(3) 0.0284(6) Uani 1 1 d . . . . .
C2 C 0.6185(5) 0.6689(4) 0.8700(4) 0.0274(6) Uani 1 1 d . . . . .
N3 N 0.6913(5) 0.6438(4) 1.0037(3) 0.0336(7) Uani 1 1 d . . . . .
H3A H 0.699(6) 0.542(6) 1.005(5) 0.040(11) Uiso 1 1 d . . . . .
H3B H 0.730(6) 0.726(6) 1.084(6) 0.042(12) Uiso 1 1 d . . . . .
O1 O 0.7777(4) 1.2918(3) 1.0276(3) 0.0334(5) Uani 1 1 d . . . . .
C3 C 0.8592(5) 1.2605(4) 1.1439(4) 0.0290(7) Uani 1 1 d . . . . .
N4 N 0.8349(4) 1.0971(4) 1.1601(4) 0.0320(6) Uani 1 1 d . . . . .
H4 H 0.767(6) 1.025(6) 1.084(6) 0.040(12) Uiso 1 1 d . . . . .
C4 C 0.9037(5) 1.0483(4) 1.2885(4) 0.0315(7) Uani 1 1 d . . . . .
O2 O 0.8607(4) 0.9047(3) 1.3010(3) 0.0391(6) Uani 1 1 d . . . . .
N5 N 1.0219(4) 1.1676(4) 1.3995(4) 0.0327(6) Uani 1 1 d . . . . .
H5 H 1.061(9) 1.136(8) 1.487(8) 0.073(17) Uiso 1 1 d . . . . .
C5 C 1.0604(5) 1.3290(4) 1.3879(4) 0.0303(7) Uani 1 1 d . . . . .
H5A H 1.1435 1.4073 1.4688 0.036 Uiso 1 1 calc R U . . .
C6 C 0.9850(5) 1.3808(4) 1.2664(4) 0.0294(7) Uani 1 1 d . . . . .
C7 C 1.0208(5) 1.5572(4) 1.2547(4) 0.0345(7) Uani 1 1 d . . . . .
H7A H 1.1147 1.6220 1.3413 0.052 Uiso 1 1 calc R U . . .
H7B H 0.9103 1.6091 1.2582 0.052 Uiso 1 1 calc R U . . .
H7C H 1.0607 1.5562 1.1570 0.052 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni S2 2.1541(8) . ?
Ni S2 2.1541(8) 2_666 ?
Ni S1 2.1660(8) 2_666 ?
Ni S1 2.1660(8) . ?
S1 C1 1.739(3) . ?
S2 C2 1.729(3) . ?
N1 C1 1.331(4) . ?
N1 H1A 0.93(5) . ?
N1 H1B 0.92(6) . ?
C1 N2 1.334(4) . ?
N2 C2 1.350(4) . ?
C2 N3 1.329(4) . ?
N3 H3A 0.86(5) . ?
N3 H3B 0.86(5) . ?
O1 C3 1.238(4) . ?
C3 N4 1.396(4) . ?
C3 C6 1.444(5) . ?
N4 C4 1.373(4) . ?
N4 H4 0.86(5) . ?
C4 O2 1.241(4) . ?
C4 N5 1.363(5) . ?
N5 C5 1.375(4) . ?
N5 H5 0.91(7) . ?
C5 C6 1.349(5) . ?
C5 H5A 0.9500 . ?
C6 C7 1.493(5) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
S2 Ni S2 180.0 . 2_666 ?
S2 Ni S1 85.50(3) . 2_666 ?
S2 Ni S1 94.50(3) 2_666 2_666 ?
S2 Ni S1 94.50(3) . . ?
S2 Ni S1 85.50(3) 2_666 . ?
S1 Ni S1 180.0 2_666 . ?
C1 S1 Ni 115.11(11) . . ?
C2 S2 Ni 113.13(11) . . ?
C1 N1 H1A 120(3) . . ?
C1 N1 H1B 121(3) . . ?
H1A N1 H1B 116(4) . . ?
N1 C1 N2 115.8(3) . . ?
N1 C1 S1 113.2(2) . . ?
N2 C1 S1 131.0(2) . . ?
C1 N2 C2 123.6(3) . . ?
N3 C2 N2 115.2(3) . . ?
N3 C2 S2 112.9(2) . . ?
N2 C2 S2 131.8(2) . . ?
C2 N3 H3A 117(3) . . ?
C2 N3 H3B 121(3) . . ?
H3A N3 H3B 122(4) . . ?
O1 C3 N4 119.4(3) . . ?
O1 C3 C6 124.9(3) . . ?
N4 C3 C6 115.7(3) . . ?
C4 N4 C3 125.4(3) . . ?
C4 N4 H4 119(3) . . ?
C3 N4 H4 115(3) . . ?
O2 C4 N5 122.8(3) . . ?
O2 C4 N4 121.7(3) . . ?
N5 C4 N4 115.5(3) . . ?
C4 N5 C5 122.1(3) . . ?
C4 N5 H5 115(4) . . ?
C5 N5 H5 123(4) . . ?
C6 C5 N5 122.8(3) . . ?
C6 C5 H5A 118.6 . . ?
N5 C5 H5A 118.6 . . ?
C5 C6 C3 118.1(3) . . ?
C5 C6 C7 123.4(3) . . ?
C3 C6 C7 118.5(3) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A S1 0.93(5) 2.66(5) 3.586(3) 174(4) 2_676
N1 H1B O1 0.92(6) 1.94(6) 2.855(4) 171(5) .
N3 H3A O1 0.86(5) 2.26(5) 3.101(4) 168(4) 1_545
N3 H3B O2 0.86(5) 2.17(5) 3.020(4) 169(4) .
N4 H4 N2 0.86(5) 2.24(5) 3.088(4) 170(4) .
N5 H5 O2 0.91(7) 2.04(7) 2.954(4) 172(6) 2_778

_refine_diff_density_max         0.495
_refine_diff_density_min         -0.755
_refine_diff_density_rms         0.091

_shelxl_version_number           2013-3

_database_code_depnum_ccdc_archive 'CCDC 956094'
